BR112015026644B1 - TETRAZOLINONE COMPOUND AND USE OF THE SAME - Google Patents

Abstract

tetrazolinone compound and its use. the invention relates to a tetrazolinone compound of formula (1): wherein r1 and r2 each independently represents a hydrogen atom, etc .; r3 represents a c1-c6 alkyl group, etc .; r4, r5, and r6 each independently represents a hydrogen atom, etc .; a represents a c6-c16 aryl group optionally having one or more atoms or groups selected from the p group, etc .; q represents the following group q1, etc .; and x represents an oxygen atom or a sulfur atom, having excellent pest control activity.

Description

Technical Field

[001] The present invention relates to the tetrazolinone compounds and applications thereof.

Background Technique

[002] So far, several chemicals have been developed in order to control pests and are supplied in use in practice, but in some cases, these chemicals may not exercise enough activity.

e fórmula (B):

(veja WO 96/36229 A).[003] Meanwhile, compounds represented by the formula (A) have been known as compounds having a tetrazolinone ring:

and formula (B):

(see WO 96/36229 A).

[004] The present invention provides compounds having excellent pest control activity.

Description of the Invention

[005] The present inventors studied intensively in order to discover compounds having excellent pest control activity, and found that a tetrazolinone compound represented by formula (1) has excellent pest control activity, thereby completing the present invention.

[006] The present invention includes the following [1] to [5],

em que[007] [1] A tetrazolinone compound represented by formula (1):

on what

[008] R1 and R2 each independently represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group;

[009] R3 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a C1-C6 group alkylthio, a C2-C6 alkynyl group, a nitro group, a cyano group, an aminocarbonyl group optionally having a C1-C6 alkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6 halocycloalkyl group, a C1-C6 haloalkoxy group, a C1- C6 haloalkylthio group, a C3-C6 cycloalkyloxy group, a C3-C6 halo-cycloalkyloxy group, a C3-C6 cycloalkylthio group, a C3-C6 alkenyloxy group, a C3- C6 alkynyloxy, a C3-C6 haloalkenyloxy group, a C3-C6 haloalkynyloxy group, a C3-C6 alkenylthio group, a C3-C6 alkynylthio group, a C3-C6 haloalkenylthio group, a C3-C6 haloalkylthio group, a C3-C6 haloalkynyl group alkylcarbonyl, a C2-C6 haloalkylcarbonyl group, a C2-C6 alkylcarbonyloxy group, a C2-C6 alkylcarbonylthio group, a C2-C6 alkoxycarbonyl group, a hi group droxyl, a thiol, an amino optionally having a C1-C6 alkyl group, pentafluorosulfanyl, a C3-C9 trialkylsilyl group, a C5-C14 trialkylsilylethynyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C2-C5 alkoxyalkyl group, or a C2-C5 alkylthioalkyl group;

[0010] R4, R5, and R6 each independently represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C5 cycloalkyl group, a C3-C5 halocycloalkyl group , a C1-C4 alkoxy group, or a C1-C4 haloalkoxy group;

[0011] R7 represents a C1-C6 alkyl group, a hydrogen atom, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkoxyalkyl group, a C3-C6 group cycloalkyl, or a C3-C6 halocycloalkyl group;

[0012] A represents a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, a C3-C12 cycloalkyl group optionally having one or more atoms or groups selected from Group P, a C2-C9 heterocyclyl group optionally having one or more atoms or groups selected from Group P (provided that the heterocyclyl C2-C9 group has, as a ring constituent atom, one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom and, when the C2-C9 heterocyclyl group has two or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, each atom can be equal to, or different from, hair minus one other, and also the carbon or nitrogen atom that constitutes the C2-C9 heterocyclyl ring is linked to Q), or a C3-C12 cycloalkenyl group optionally having one or more atoms or groups selected from Group P (provided that the group C6-C16 aryl, C3-C12 cycloalkyl group, C2-C9 heterocyclyl group, and C3-C12 cycloalkenyl group optionally have one or more atoms or groups selected from Group P and, when these groups have two or more atoms or groups selected from Group P, each atom or group can be equal to or different from at least one other atom or group);

[0013] Q represents the following group Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, or Q12 {the symbol # represents an A-binding site, and the symbol • represents a binding site to an oxygen atom};

[0014] R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31 , R32, R33, R34, R35, and R36 each independently representing a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more atoms or groups selected from Group P1, a C3-C6 cycloalkyl group optionally having one or more atoms or groups selected from Group P1, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a cyano group, a nitro group, an amino group, a hydroxy group, a thiol group, a C2 group -C6 alkenyl, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, an amino group optionally having a C1-C6 alkyl group, an amino group optionally having a C1-C6 haloal group - kyl, a C1-C6 alkylthio group, a C1-C6 haloalkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a pentafluorosulfanyl group, a C3-C9 trialkylsilyl group, a C2-C6 alkylcarbonyl group, a C2-C6 alkoxycarbonyl group, or an aminocarbonyl group optionally having a C1-C6 alkyl group; and

[0015] X represents an oxygen atom or a sulfur atom:

[0016] Group P: Group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C1-C6 haloalkyl group a C3-C6 cycloalkyloxy group, a C3-C6 halocycloalkyloxy group, a C3-C6 cycloalkylthio group, a C3-C6 alkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6 haloalkenyloxy group, a C3-C6 haloalkyloxy group, a C3-C6 haloalkyloxy group , a C3-C6 alkenylthio group, a C3-C6 alkynylthio group, a C3-C6 haloalkenylthio group, a C3-C6 haloalkylthio group, a C2-C6 alkylcarbonyl group, a C2-C6 haloalkylcarbonyl group, a C2-C6 alkylcarbonyl group a C2-C6 alkylcarbonylthio group, a hydroxycarbonyl group, a formyl group, a C2-C6 alkoxycarbonyl group, a nitro group, a cyano group, the hydroxyl, a group C6-C16 aryl, a C6-C16 haloaryl group, a C6-C16 aryloxy group, a C6-C16 haloaryloxy group, a C6-C16 arylthio group, a C6-C16 haloaryl group, a C7-C18 aralkyl group, a C7 group -C18 haloaralkyl, a C7-C18 arylalkoxy group, a C7-C18 haloarylalkoxy group, a thiol group, a pentafluorosulfanyl group, a C3-C12 trialkylsilyl group, a C5-C14 trialkylsilylethinyl group, a C1-C6 alkylsulfon group -C6 haloalkylsulfonyl, a C6-C16 arylsulfonyl group, a 06- C16 haloarylsulfonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, a C6-C16 arylsulfinyl group, a C6-C16 arylsulfinyl group, a C6-C16 arylsulfinyl group, a C6-halo group amino optionally having a C1-C6 alkyl group, an aminosulfonyl group optionally having a C1- C6 alkyl group and / or a C6-C12 group, and an aminocarbonyl group optionally having a C1-C6 alkyl group; and

[0017] Group P1: Group consisting of a halogen atom, a cyano group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a group C1-C4 alkylthio, and a C1-C4 haloalkylthio group.

[0018] [2] The tetrazolinone compound according to [1], where Q is Q1.

[0019] [3] The tetrazolinone compound according to [1], where Q is Q2.

[0020] [4] The tetrazolinone compound according to [1], where Q is Q3.

[0021] [5] The tetrazolinone compound according to [1], where Q is Q4.

[0022] [6] The tetrazolinone compound according to [1], where Q is Q5.

[0023] [7] The tetrazolinone compound according to [1], where Q is Q6.

[0024] [8] The tetrazolinone compound according to [1], where Q is Q7.

[0025] [9] The tetrazolinone compound according to [1], where Q is Q8.

[0026] [10] The tetrazolinone compound according to [1], where Q is Q9.

[0027] [11] The tetrazolinone compound according to [1], where Q is Q10.

[0028] [12] The tetrazolinone compound according to [1], where Q is Q11.

[0029] [13] The tetrazolinone compound according to [1], where Q is Q12.

[0030] [14] The tetrazolinone compound according to any one of [1] to [13], wherein R1, R2, R4, R5, and R6 are hydrogen atoms;

[0031] R7 is a methyl group; and

[0032] X is an oxygen atom.

[0033] [15] The tetrazolinone compound according to any one of [1] to [14], where A is a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P (provided that when the C6-C16 aryl group has two or more atoms or groups selected from Group P, each atom or group can be equal to or different from at least one other atom or group).

em que[0034] [16] The tetrazolinone compound according to any one of [1] to [15], where A is of formula (2):

on what

[0035] R37, R38, R39, R40, and R41 each independently represents a halogen atom, a hydrogen atom, a C1- C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a group C1-C6 alkylthio, a C1-C6 haloalkylthio group, a C3-C6 cycloalkyloxy group, a C3-C6 halocycloalkyloxy group, a C3-C6 cycloalkylthio group, a C3-C6 alkenyloxy group, a C3-C6 alkynoxy group, a C3 group -C6 haloalkenyloxy, a C3-C6 haloalkyloxy group, a C3-C6 alkenylthio group, a C3-C6 alkynylthio group, a C3-C6 haloalkenylthio group, a C3-C6 haloalkylthio group, a C2-C6 alkoxyalkyl group, a group C2-C6 haloalkylcarbonyl, a C2-C6 alkylcarbonyloxy group, a C2-C6 alkylcarbonylthio group, a hydroxycarbonyl group, a formyl group, a C2-C6 alkoxy group bonila, a nitro group, a cyano group, a hydroxyl group, a C6-C16 aryl group, a C6-C16 haloaryl group, a C6-C16 aryloxy group, a C6-C16 haloaryloxy group, a C6-C16 aryl group, a C6-C16 haloaryl group, a C7-C18 aralkyl group, a C7-C18 haloaralkyl group, a C7-C18 arylalkoxy group, a C7-C18 haloarylalkoxy group, a thiol group, a pentafluorosulfanyl group, a C3-C12 trialkylsilyl group C5-C14 trialkylsilylethynyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C6-C16 arylsulfonyl group, a C6-C16 haloarylsulfonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsin group a C6-C16 arylsulfinyl group, a C6-C16 halo-arylsulfinyl group, an aminosulfonyl group optionally having a C1-C6 alkyl group and / or a C6-C12 aryl group, or an aminocarbonyl group optionally having a C1-C6 group alkyl.

[0036] [17] The tetrazolinone compound according to any one of [1], [2], [14], [15], or [16], where Q is Q1;

[0037] R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C1-C2 group alkylthio, a C2-C3 alkynyl group, a C1-C3 haloalkoxy group, or a C1-C2 haloalkylthio group;

[0038] R8, R9, and R10 each independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having a group selected from Group P1, a C3-C6 cycloalkyl group optionally having a group selected from Group P1, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group;

[0039] R37, R38, R39, R40, and R41 each independently represent a halogen atom, a hydrogen atom, a C1- C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C3-C6 cycloalkyloxy group, a C2-C6 alkylcarbonyloxy group, a formyl group, a C2-C6 alkoxycarbonyl group, a C2-C6 alkylcarbonyl group, a nitro group cyano group, hydroxyl group, C6-C16 aryloxy group, C1-C6 alkylsulfonyl group, C1-C6 alkylsulfinyl group, aminosulfonyl group optionally having a C1-C6 alkyl group and / or a C6-C12 aryl group, or an aminocarbonyl group optionally having a C1-C6 alkyl group.

[0040] [18] The tetrazolinone compound according to any one of [1], [2], and [14] to [17], where R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group , a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C2-C3 alkynyl group, or a C1-C3 haloalkoxy group; and

[0041] R37, R38, R39, R40, and R41 each independently represent a halogen atom, a hydrogen atom, a C1- C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, or a C1-C3 haloalkoxy group.

[0042] [19] The tetrazolinone compound according to any one of [1], [2], and [14] to [18], where R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, an ethyl group, or a methoxy group;

[0043] R37 is a methoxy group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a bromine atom; and

[0044] R38, R39, R40, and R41 each independently represents a hydrogen atom or a fluorine atom.

[0045] [20] The tetrazolinone compound according to any one of [1], [3], [14], [15], and [16], where Q is Q2;

[0046] R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C1-C2 group alkylthio, a C2-C3 alkynyl group, a C1-C3 haloalkoxy group, or a C1-C2 haloalkylthio group;

[0047] R11, R12, R13 and R14 each independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having a group selected from Group P1, a C3-C6 cycloalkyl group optionally having a group selected from Group P1, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group;

[0048] R37, R38, R39, R40, and R41 each independently represents a halogen atom, a hydrogen atom, a C1- C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C3-C6 cycloalkyloxy group, a C2-C6 alkylcarbonyloxy group, a formyl group, a C2-C6 alkoxycarbonyl group, a C2-C6 alkylcarbonyl group, a nitro group cyano group, hydroxyl group, C6-C16 aryloxy group, C1-C6 alkylsulfonyl group, C1-C6 alkylsulfinyl group, aminosulfonyl group optionally having a C1-C6 alkyl group and / or a C6-C12 aryl group, or an aminocarbonyl group optionally having a C1-C6 alkyl group.

[0049] [21] The tetrazolinone compound according to any one of [1], [3], [14] to [16], and [20], where R3 is a C1-C3 alkyl group, a group C3-C4 cycloalkyl, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C2-C3 alkynyl group, or a C1-C3 haloalkoxy group; and

[0050] R37, R38, R39, R40, and R41 each independently represents a halogen atom, a hydrogen atom, a C1- C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, or a C1-C3 haloalkoxy group.

[0051] [22] The tetrazolinone compound according to any one of [1], [3], [14] to [16], [20], and [21], where R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, an ethyl group, or a methoxy group;

[0052] R37 is a methoxy group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a bromine atom; and

[0053] R38, R39, R40, and R41 each independently represent a hydrogen atom or a fluorine atom.

[0054] [23] The tetrazolinone compound according to any one of [1] to [14], where A is a C3-C12 cycloalkyl group optionally having one or more atoms or groups selected from Group P, a group C2 -C9 heterocyclyl optionally having one or more atoms or groups selected from Group P as long as the C2-C9 heterocyclyl group has, as a ring constituent atom, one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom , and a sulfur atom, and when the C2-C9 heterocyclyl group has two or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, each atom can be equal to, or different of at least one other atom, and the carbon or nitrogen atom that forms the ring of the C2-C9 heterocyclyl group is attached to Q, or a C3-C12 cycloalkenyl group optionally having one or more atoms or groups selected from Group P, provided that when the C3-C12 cycloalkyl group, the C2-C9 heterocyclyl group, and C3-C12 cycloalkenyl group have two or more atoms or groups selected from Group P, each atom or group can be equal to, or different from, at least one other atom or group.

[0055] [24] The tetrazolinone compound according to any one of [1] to [14], wherein A is a C2-C9 heteroaryl group optionally having one or more atoms or groups selected from Group P.

[0056] [25] A pest control agent comprising the tetrazolinone compound according to any one of [1] to [24],

[0057] [26] A method for pest control, which comprises treating plants or soil with an effective amount of the tetrazolinone compound according to any of [1] to [24],

[0058] [27] Use of the tetrazolinone compound according to any of [1] to [24] for pest control.

em que[0059] [28] A tetrazolinone compound represented by the formula (3):

on what

[0060] R1 and R2 each independently represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group;

[0061] R3 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a C1-C6 group alkylthio, a C2-C6 alkynyl group, a nitro group, a cyano group, an aminocarbonyl group optionally having a C1-C6 alkyl group, a C2-C6 haloalkenyl group, a C2-C6 haloalkynyl group, a C3-C6 halocycloalkyl group, a C1-C6 haloalkoxy group, a C1- C6 haloalkylthio group, a C3-C6 cycloalkyloxy group, a C3-C6 halo-cycloalkyloxy group, a C3-C6 cycloalkylthio group, a C3-C6 alkenyloxy group, a C3- C6 alkynyloxy, a C3-C6 haloalkenyloxy group, a C3-C6 haloalkynyloxy group, a C3-C6 alkenylthio group, a C3-C6 alkynylthio group, a C3-C6 haloalkenylthio group, a C3-C6 haloalkylthio group, a C3-C6 haloalkynyl group alkylcarbonyl, a C2-C6 haloalkylcarbonyl group, a C2-C6 alkylcarbonyloxy group, a C2-C6 alkylcarbonylthio group, a C2-C6 alkoxycarbonyl group, a h group idroxyl, a thiol group, an amino group optionally having a C1-C6 alkyl group, a pentafluorosulfanyl group, a C3-C9 trialkylsilyl group, a C5-C14 trialkylsilylethynyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C2-C5 alkoxyalkyl group, or a C2-C5 alkylthioalkyl group;

[0062] R4, R5, and R6 each independently represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C5 cycloalkyl group, a C3-C5 halocycloalkyl group , a C1-C4 alkoxy group, or a C1-C4 haloalkoxy group;

[0063] R7 represents a C1-C6 alkyl group, a hydrogen atom, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkoxyalkyl group, a C3-C6 group cycloalkyl, or a C3-C6 halocycloalkyl group;

[0064] Zx represents a halogen atom;

[0065] Q represents the following group Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, or Q12; and X represents an oxygen or sulfur atom

[0066] [29] The tetrazolinone compound according to [28], wherein Q is Q1, Q2, or Q4;

[0067] R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, an ethyl group, or a methoxy group;

[0068] R1, R2, R4, R5, and R6 are hydrogen atoms;

[0069] R7 is a methyl group; and

[0070] X is an oxygen atom.

[0071] [30] The tetrazolinone compound according to any one of [1], [2], and [14] to [18], where R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, an ethyl group, or a methoxy group;

[0072] R37 is a methoxy group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a bromine atom;

[0073] R38, R39, and R40 each independently represents a hydrogen atom or a fluorine atom; and

[0074] R41 is a hydrogen atom, a methoxy group, or an ethoxy group.

[0075] [31] The tetrazolinone compound according to any one of [1], [2], [14], and [24], where Q is Q1; and

em que[0076] A is formula (4):

on what

[0077] R42, R43, R44, and R45 each independently represents a halogen atom, a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2- C6 haloalkenyl, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1 group -C6 alkylthio, a C1-C6 haloalkylthio group, a C3-C6 cycloalkyloxy group, a C3-C6 halocycloalkyloxy group, a C3-C6 cycloalkylthio group, a C3-C6 alkenyloxy group, a C3-C6 alkynoxy group, a group C3-C6 haloalkenyloxy, a C3-C6 haloalkynyloxy group, a C3-C6 alkenylthio group, a C3-C6 alkynylthio group, a C3-C6 haloalkenylthio group, a C3-C6 haloalkylthio group, a C2-C6 alkoxyalkyl group, C2-C6 haloalkylcarbonyl group, a C2-C6 alkylcarbonyloxy group, a C2-C6 alkylcarbonylthio group, a hydroxycarbonyl group, a formyl group, a C2-C6 alkoxycarbon group ila, a nitro group, a cyano group, a hydroxyl group, a C6-C16 aryl group, a C6-C16 haloaryl group, a C6-C16 aryloxy group, a C6-C16 haloaryloxy group, a C6-C16 arylthio group, a C6-C16 haloaryl group, a C7-C18 aralkyl group, a C7-C18 haloaralkyl group, a C7-C18 arylalkoxy group, a C7-C18 haloarylalkoxy group, a thiol group, a pentafluorosulfanyl group, a C3-C12 trialkylsilyl group C5-C14 trialkylsilylethynyl group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C6-C16 arylsulfonyl group, a C6-C16 haloarylsulfonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsin group a C6-C16 arylsulfinyl group, a C6-C16 halo-arylsulfinyl group, an aminosulfonyl group optionally having a C1-C6 alkyl group and / or a C6-C12 aryl group, or an aminocarbonyl group optionally having a C1-C6 group alkyl.

[0078] [32] The tetrazolinone compound according to any one of [1], [2], [14], [24], and [31], where R3 is a methyl group, a cyclopropyl group, a chlorine atom, bromine atom, ethyl group, or methoxy group;

[0079] R42 is a hydrogen atom, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, or a trifluoromethyl group;

[0080] R43 and R44 each independently represents a hydrogen atom or a fluorine atom; and

[0081] R45 is a hydrogen atom, a methoxy group, or an ethoxy group.

[0082] [33] The tetrazolinone compound according to any one of [1], [3], [14], and [24], where Q is Q2; and A is of formula (4).

[0083] [34] The tetrazolinone compound according to any one of [1], [3], [14], [24], and [33], where R3 is a methyl group, a cyclopropyl group, a chlorine atom, bromine atom, ethyl group, or methoxy group;

[0084] R42 is a hydrogen atom, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, or a trifluoromethyl group;

[0085] R43 and R44 each independently represents a hydrogen atom or a fluorine atom; and

[0086] R45 is a hydrogen atom, a methoxy group, or an ethoxy group.

[0087] According to the present invention, pests can be controlled.

Mode of Carrying Out the Invention

[0088] The compound of the present invention is a tetrazolinone compound represented by formula (1).

[0089] A pest control agent containing the present compound is referred to as the present control agent.

[0090] The present invention also provides a tetrazolinone compound represented by formula (3) to be used in the production of the present compound (hereinafter referred to as the present tetrazolinone compound X), and the present tetrazolinone compound X has control activity against pests.

[0091] Substitutes as used here will be mentioned in detail below.

[0092] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0093] The C1-C6 alkyl group represents a straight or branched alkyl group having 1 to 6 carbon atoms, and examples of which include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0094] The C1-C6 haloalkyl group represents a group in which at least one hydrogen atom of a C1-C6 alkyl group is replaced by a halogen atom, and examples thereof include a monofluoromethyl group, a monochloromethyl group dichloromethyl, a difluoromethyl group, a trifluoromethyl group, a trichloromethyl group, a tribromomethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichlorethyl group, a pentafluoroethyl group, a chlorofluoromethyl group, a dichlorofluoromethyl group, a chloro-difluoromethyl group, a 2,2-difluoroethyl group, a 2-fluoropropyl group, a 3-fluoropropyl group, a 2,2-difluoropropyl group, a 3,3,3-trifluoropropyl group, a 3- (fluoromethyl group ) -2-fluoroethyl, a 4-fluorobutyl group, and a 2,2-difluorohexyl group.

[0095] The C2-C4 alkenyl group represents a linear or branched alkenyl group having 2 to 6 carbon atoms, and examples thereof include a vinyl group, a 1-propenyl group, an isopropenyl group, a 2-propenyl group , a 1-butenyl group, a 1-methyl-1-propenyl group, a butenyl group, a 1-methyl-2-propenyl group, a 3-butenyl group, a 2-methyl-1-propenyl group, a group 2 -methyl-2-propenyl, a 1,3-butadienyl group, a 1-pentenyl group, a 1-ethyl-2-propenyl group, a 2-pentenyl group, a 1-methyl-1-butyl group, a group 3 -pentenyl, a 1-methyl-2-butenyl group, a 4-pentenyl group, a 1-methyl-3-butenyl group, a 1-hexenyl group, and a 5-hexenyl group.

[0096] The C2-C6 haloalkenyl group represents a group in which at least one hydrogen atom of a linear or branched alkenyl group having 2 to 6 carbon atoms is replaced by a halogen atom, and examples of the same include a group 2 -chlorovinyl, a 2-bromovinyl group, a 2-iodovinyl group, a 3-chloro-2-propenyl group, a 3-bromo-2-propenyl group, a 1-chloromethylvinyl group, a 2-bromo-1-methylvinyl group , a 1-trifluoromethylvinyl group, a 3,3,3-trichloro-1-propenyl group, a 3-bromo-3,3-difluoro-1-propenyl group, a 2,3,3,3-tetrachlor-1 group -propenyl, a 1-trifluoromethyl-2,2-difluorovinyl group, a 2-chloro-2-propenyl group, and a 3,3-difluoro-2-propenyl group.

[0097] The C2-C6 alkynyl group represents a linear or branched alkynyl group having 2 to 6 carbon atoms, and examples thereof include an ethynyl group, a propargyl group, a 1-butin-3-yl group, a 3 group -methyl-1-butin-3-yl, a 2-butynyl group, a 3-butynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, and a group 5-hexynyl.

[0098] The C2-C6 haloalkynyl group represents a group in which at least one hydrogen atom of a linear or branched alkynyl group having 2 to 6 carbon atoms is replaced by a halogen atom, and examples of the same include a fluoroethynyl group , a 3-chloro-2-propynyl group, a 3-bromo-2-propynyl group, a 3-iodo-2-propynyl group, a 3-chloro-1-propynyl group, a 5-chloro-4-pentynyl group , a 3,3,3-trifluoro-1-propynyl group, a 3-fluoro-2-propynyl group, a perfluoro-2-butynyl group, a perfluoro-2-pentynyl group, a perfluoro-3-pentynyl group, and a perfluoro-1-hexynyl group.

[0099] Examples of the C3-C6 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[00100] The C3-C6 halocycloalkyl group represents a group in which at least one hydrogen atom of a C3-C6 cycloalkyl group is replaced by a halogen atom, and examples of the same include a 2-fluorocyclopropyl group, a group 2, 2-difluorocyclopropyl, a 2-chloro-2-fluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2-dibromocyclopropyl group, a 2,2,3,3-tetrafluorocyclobutyl group, a 2-chlorocyclohexyl group, a 4,4-difluorocyclohexyl group, and a 4-chlorocyclohexyl group.

[00101] The C1-C6 alkoxy group represents a linear or branched alkoxy group having 1 to 6 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, a isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, an isoamyloxy group, a neopentyloxy group, a 2-pentyloxy group, a 3-pentyloxy group, a 2-methylbutoxy group, a hexyloxy group , an isohexyloxy group, a 3-methylpentyloxy group, and a 4-methylpentyloxy group.

[00102] The C1-C6 haloalkoxy group represents a group in which at least one hydrogen atom of a C1-C6 alkoxy group is replaced by a halogen atom, and examples thereof include a trifluoromethoxy group, a trichloromethoxy group, a chloromethoxy group, a dichloromethoxy group, a fluoromethoxy group, a difluoromethoxy group, a chlorofluoromethoxy group, a dichlorofluoromethoxy group, a chlorodifluoromethoxy group, a pentafluoroethoxy group, a penta-chloroethoxy group, a 2,2,2-trichloro group a 2,2,2-trifluoroethoxy group, a 2,2,2-tribromoethoxy group, a 2,2,2-tri-iodoethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2,2- difluoroethoxy, and a period-hexyloxy group.

The C1-C6 alkylthio group represents a straight or branched alkylthio group having 1 to 6 carbon atoms, and examples thereof include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, an isopentylthio group, a neopentylthio group, a hexylthio group, an isohexylthio group, and a sec-hexylthio group.

[00104] The C1-C6 haloalkylthio group represents a group in which at least one hydrogen atom of a C1-C6 alkylthio group is replaced by a halogen atom, and examples of the same include monofluoromethylthio, a difluoromethylthio group, a trifluoro group - methylthio, a trichloromethylthio group, a tribromomethylthio group, a triiodomethylthio group, a chlorofluoromethylthio group, a pentafluoroethylthio group, a pentachlorethylthio group, a pentabromoethylthio group, a pentatodoethylthio group, a 2,2,2-trichlorethylthio group, a 2 group , 2,2-trifluoroethylthio, a 2,2-difluoroethylthio group, a heptafluoropropylthio group, a 3,3,3-trifluoropropylthio group, a 3,3,3-trichloropropylthio group, a 2,2-difluoropropylthio group, a group 2 , 3,3-trifluoropropylthio, and a perfluorohexylthio group.

[00105] Examples of the C3-C6 cycloalkyloxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

[00106] The C3-C6 halocycloalkyloxy group represents a group in which at least one hydrogen atom of a C3-C6 cycloalkyloxy group is replaced by a halogen atom, and examples thereof include a 2-fluorocyclopropyloxy group 2,2-difluorocyclopropyloxy, a 2-chloro-2-fluorocyclopropyloxy group, a 2,2-dichlorocyclopropyloxy group, a 2,2-dibromocyclopropyloxy group, a 2,2,3,3-tetrafluorocyclobutyloxy group, a 2-chlorocyclo- hexyloxy, a 4,4-difluorocyclohexyloxy group, and a 4-chlorocyclohexyloxy group.

[00107] Examples of the C3-C6 cycloalkylthio group include a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, and a cyclohexylthio group.

The C3-C6 alkenyloxy group represents a linear or branched alkenyloxy group having 3 to 6 carbon atoms, and examples thereof include a 2-propenyloxy group, a 2-butenyloxy group, a 1-methyl-2-propenyloxy group , a 3-butenyloxy group, a 2-methyl-2-propenyloxy group, a 2-pentenyloxy group, a 3-pentenyloxy group, a 4-pentenyloxy group, a 1-methyl-3-butenyloxy group, a group 1,2 -dimethyl-2-propenyloxy, a 1,1-dimethyl-2-propenyloxy group, a 2-methyl-2-butenyloxy group, a 3-methyl-2-butenyloxy group, a 2-methyl-3-butenyloxy group, a 3-methyl-3-butenyloxy group, 1-vinyl-2-propenyloxy group, and 5-hexenyloxy group.

[00109] The C3-C6 alkynyloxy group represents a linear or branched alkynyloxy group having 3 to 6 carbon atoms, and examples of which include a propargyloxy group, a 1-butin-3-yloxy group, a 3-methyl-1 group -butin-3-yloxy, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 3-pentynyloxy group, a 4-pentynyloxy group, and a 5-hexynyloxy group.

[00110] The C3-C6 haloalkenyloxy group represents a group in which at least one hydrogen atom of a C3-C6 alkenyloxy group is replaced by a halogen atom, and examples thereof include 3-chloro-2-propenyloxy , a 3-bromo-2-propenyloxy group, a 3-bromo-3,3-difluoro-1-propenyloxy group, a 2,3,3,3-tetrachloro- 1-propenyloxy group, a 2-chloro-2 group -propenyloxy, a 3,3-difluoro-2-propenyloxy group, a 2,3,3-trichloro-2-propenyloxy group, a 3,3-dichloro-2-propenyloxy group, a 3,3-dibromo-2 group -propenyloxy, a 3-fluoro-3-chloro-2-propenyloxy group, a 4-bromo-3-chloro-3,4,4-trifluoro-1-butenyloxy group, a 1-bromomethyl-2-propenyloxy group, a 4,5,5,5-tetrafluoro-4-trifluoromethyl-2-pentenyloxy group, and a 5-bromo-4,5,5-trifluoro-4-trifluoromethyl-2-pentenyloxy group.

[00111] The C3-C6 haloalkynoxy group represents a group in which at least one hydrogen atom of a C3-C6 alkynyloxy group is replaced by a halogen atom, and examples of the same include a 3-chloro-2-propynyloxy group, a 3-bromo-2-propynyloxy group, a 3-iodo-2-propynyloxy group, a 5-chloro-4-pentynyloxy group, a 3-fluoro-2-propynyloxy group, a perfluoro-2-butynyloxy group, a group perfluoro-3-butynyloxy, a perfluoro-2-pentynyloxy group, a perfluoro-3-pentynyloxy group, a perfluoro-4-pentynyloxy group, and a perfluoro-5-hexynyloxy group.

The C3-C6 alkenylthio group represents a linear or branched alkenylthio group having 3 to 6 carbon atoms, and examples of which include 2-propenylthio, a 2-butenylthio group, a 1-methyl-2-propenylthio group, a 3-butenylthio group, a 2-methyl-2-propenylthio group, a 2-pentenylthio group, a 3-pentenylthio group, a 4-pentenylthio group, a 1-methyl-3-butenylthio group, a 1,2- dimethyl-2-propenylthio, a 1,1-dimethyl-2-propenylthio group, a 2-methyl-2-butenylthio group, a 3-methyl-2-butenylthio group, a 2-methyl-3-butenylthio group, a group 3-methyl-3-butylthio, a 1-vinyl-2-propenylthio group, and a 5-hexenylthio group.

[00113] The C3-C6 alkynylthio group represents a linear or branched C3-C6 al-quinylthio group, and examples thereof include a propargylthio group, a 1-butin-3-ylthio group, a 3-methyl-1-butin group -3-ylthio, a 2-butynylthio group, a 3-butynylthio group, a 2-pentynylthio group, a 3-pentynylthio group, a 4-pentynylthio group, and a 5-hexynylthio group.

[00114] The C3-C6 haloalkenylthio group represents a group in which at least one hydrogen atom of a C3-C6 alkenylthio group is replaced by a halogen atom, and examples thereof include a 3-chloro-2-propenylthio group, a 3-bromo-2-propenylthio group, a 3-bromo-3,3-difluoro-1-propenylthio group, a 2,3,3,3-tetrachloro-1-propenylthio group, a 2-chloro-2- group propenylthio, a 3,3-difluoro-2-propenylthio group, a 2,3,3-trichloro-2-propenylthio group, a 3,3-dichloro-2-propenylthio group, a 3,3-dibromo-2- group propenylthio, a 3-fluoro-3-chloro-2-propenylthio group, a 4-bromo-3-chloro-3,4,4-trifluoro-1-butenylthio group, a 1-bromomethyl-2-propenylthio group 3-chloro-2-butenylthio, a 4,4,4-trifluoro-2-butenylthio group, a 3,3-difluoro-2-methyl-2-propenylthio group, a 4,4-difluoro-3-methyl- 3-butenylthio, a 4,4,4-trifluoro-3-methyl-2-butenylthio group, a 3,5,5-trifluoro-2,4-pentadienylthio group, and a 4,5,5,5-tetrafluoro group -4-trifluoromethyl I-2-pentylthio.

[00115] The C3-C6 haloalkylthio group represents a group in which at least one hydrogen atom of a C3-C6 alkynylthio group is replaced by a halogen atom, and examples thereof include a 3-chloro-2-propynylthio group, a 3-bromo-2-propynylthio group, a 3-iodo-2-propynylthio group, a 5-chloro-4-pentynylthio group, a 3-fluoro-2-propynylthio group, a perfluoro-2-butynylthio group, a group perfluoro-3-butynylthio, a perfluoro-2-pentynylthio group, a perfluoro-3-pentynylthio group, a perfluoro-4-pentynylthio group, and a perfluoro-5-hexynylthio group.

[00116] The C2-C6 alkylcarbonyl group represents a straight or branched alkylcarbonyl group, in which the number of carbon atoms including carbonyl carbon atoms is 2 to 6, and examples of which include an acetyl, propionyl group , a butanoyl group, a pentanoyl group, and a hexanoyl group.

[00117] The C2-C6 haloalkylcarbonyl group represents a group in which at least one hydrogen atom of a C2-C6 alkylcarbonyl group is replaced by a halogen atom, and examples thereof include trichloroacetyl, a fluoroacetyl group, a difluoroacetyl group, a trifluoroacetyl group, a pentafluoropropionyl group, a pentachloropropionyl group, a pentabromopropionyl group, a pentaiodopropionyl group, a 3,3,3-trichloropropionyl group, a 3,3,3-trifluoropropionyl group, a 4,4 group , 4-trifluorobutanoyl, a 4,4,4-trichlorobutanoyl group, a nonafluoropentanoyl group, and a perfluorohexanoyl group.

[00118] The C2-C6 alkylcarbonyloxy group represents a linear or branched alkylcarbonyloxy group in which the number of carbon atoms including carbonyl carbon atoms is 2 to 6, and examples of which include an acetoxy group, a propionyloxy group, a group butanoyloxy, a pentanoyloxy group, and a hexanoyloxy group.

The C2-C6 alkylcarbonylthio group represents a linear or branched alkylcarbonylthio group in which the number of carbon atoms including carbonyl carbon atoms is 2 to 6, and examples thereof include an acetylthio group, a propionylthio group, a butanoylthio group, a pentanoylthio group, and a hexaneylthio group.

[00120] The C2-C6 alkoxycarbonyl group represents a linear or branched alkoxycarbonyl group in which the number of carbon atoms including carbonyl carbon atoms is 2 to 6, and examples thereof include methoxycarbonyl, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, an isobutyloxycarbonyl group, a sec-butyloxycarbonyl group, a tert-butyloxycarbonyl group, a pentyloxycarbonyl group, an isoamyloxycarbonyl group, a neopentyloxycarbonyl group, a 2-group , a 3-pentyloxycarbonyl group, and a 2-methylbutyloxycarbonyl group.

[00121] The aminocarbonyl group optionally having a C1- C6 alkyl group represents an aminocarbonyl group in which one or two hydrogen atoms in nitrogen, each independently can be replaced by a C1-C6 alkyl group, and examples of the same include a group aminocarbonyl, a methylaminocarbonyl group, an ethylaminocarbonyl group, a propylaminocarbonyl group, an isopropylaminocarbonyl group, a butylaminocarbonyl group, a dimethylaminocarbonyl group, a diethylaminocarbonyl group, a dipropylaminocarbonyl group, a diisopropylaminocarbonyl group, a hexisopropylaminocarbonyl group, a hexyl group.

[00122] Examples of the C6-C16 aryl group include a phenyl group, a naphthyl group, an acenaphthyl group, a phenanthryl group, an anthryl group, and a pyrenyl group.

[00123] The C6-C16 aryl group optionally having one or more atoms or groups selected from Group P represents a C6-C16 aryl group in which hydrogen atoms of a C6-C16 aryl group are optionally substituted by one or more selected atoms or groups of Group P and, when the number of atoms or groups selected from Group P is 2 or more, each atom or group can be equal to, or different from, at least one other atom or group. Examples of the C6-C16 aryl group optionally having one or more atoms or groups selected from Group P include phenyl, a 4-chlorophenyl group, a 4-bromophenyl group, a 4-fluorophenyl group, a 4-methylphenyl group, a group 4 -trifluoromethylphenyl, a 4-methoxyphenyl group, a 4-trifluoromethoxyphenyl group, a 4-cyanophenyl group, a 4-nitrophenyl group, a 4-dimethylaminophenyl group, a 4-methylthiophenyl group, a 3-fluorophenyl group, a 3-methoxyphenyl group , a 3,4,5-trifluorophenyl group, a 3-fluoro-4-methoxyphenyl group, and a 2-fluoro-4-methoxyphenyl group.

[00124] The C6-C16 haloaryl group represents a group in which at least one hydrogen atom of a C6-C16 aryl group is replaced by a halogen atom, and examples of the same include a 2-fluorophenyl group, a 3- group fluorophenyl, a 4-fluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2-bromophenyl group, a 3-bromophenyl group, a 4-bromophenyl group, a 2-iodophenyl group, a 3-iodophenyl group, a 4-iodophenyl group, a 2,4-difluorophenyl group, a 2,5-difluorophenyl group, a 2,6-difluorophenyl group, a 3,5-difluorophenyl group, a 2,4- dichlorophenyl, a 2,5-dichlorophenyl group, a 2,6-dichlorophenyl group, a 3,5-dichlorophenyl group, a 2,4,6-trifluorophenyl group, a penta-fluorophenyl group, and a 6-fluoro-1 group - pyrenyl.

[00125] Examples of the C6-C16 aryloxy group include phenyloxy, a naphthyloxy group, an acenaphthyloxy group, a phenanthryloxy group, an anthryloxy group, and a pyrenyloxy group.

[00126] The C6-C16 haloaryloxy group represents a group in which at least one hydrogen atom of a C6-C16 aryloxy group is replaced by a halogen atom, and examples thereof include a 2-fluorophenyloxy group, a 3- group fluorophenyloxy, a 4-fluorophenyloxy group, a 2-chlorophenyloxy group, a 3-chlorophenyloxy group, a 4-chlorophenyloxy group, a 2-bromophenyloxy group, a 3-bromophenyloxy group, a 4-bromophenyloxy group, a 2-iodophenyl group a 3-iodophenyloxy group, a 4-iodophenyloxy group, a 2,4-difluorophenyloxy group, a 2,5-dichlorophenyloxy group, a 2,4,6-trifluorophenyloxy group, a 2,3,4-trichlorophenyloxy group, a group pentafluoro-phenyloxy, a pentachlorophenyloxy group, a 2-bromo-4-fluorophenyloxy group, a 2-chloro-3-fluorophenyloxy group, a 2-fluoro-1-naphthyloxy group, and a 6-fluoro-1-pyrenyloxy group.

Examples of the C6-C16 arylthio group include a phenylthio group, a naphthylthio group, an acenaphthyl group, a phenanthylthio group, an anthylthio group, and a pyrenylthio group.

[00128] The C6-C16 haloarylthio group represents a group in which at least one hydrogen atom of a C6-C16 arylthio group is replaced by a halogen atom, and examples thereof include a 2-fluorophenylthio group, a 3- fluorophenylthio, a 4-fluorophenylthio group, a 2-chlorophenylthio group, a 3-chlorophenylthio group, a 4-chlorophenylthio group, a 2-bromophenylthio group, a 3-bromophenylthio group, a 4-bromophenylthio group, a 2-iodophenylthio group, a 3-iodophenylthio group, a 4-iodophenylthio group, a 2,4-difluorophenylthio group, a 2,5-dichlorophenylthio group, a 2,3,4-trifluorophenylthio group, a pentachlorophenylthio group, a 2-bromo-3- group fluorophenylthio, a 2-chloro-4-fluorophenylthio group, a 3-chloro-4-fluorophenylthio group, a 3-fluoro-1-naphthylthio group, and a 6-fluoro-1-pyrenylthio group.

[00129] Examples of the C7-C18 aralkyl group include a benzyl group, a phenethyl group, a 3-phenylpropyl group, a 4-phenylbutyl group, a 5-phenylpentyl group, a 6-phenylhexyl group, a 7-phenyl group -heptila, an 8-phenyloctyl group, a 9-phenylnonyl group, a 10-phenyldecyl group, an 11-phenylundecyl group, a 12-phenyldodecyl group, a 1-naphthylmethyl group, a 2- (1-naphthyl) ethyl group, a 3- (1- naphthyl) propyl group, a 4- (1-naphthyl) butyl group, a 2-naphthylmethyl group, a 2- (2-naphthyl) ethyl group, a 3- (2-naphthyl) propyl group, a 4- (2-naphthyl) butyl group, a 1-anthrylmethyl group, a 2- (1-anthryl) ethyl group, a 3- (1-anthryl) propyl group, and a 4- (9-anthryl) butyl group .

[00130] The C7-C18 haloaralkyl group represents a group in which at least one hydrogen atom of the aryl and / or alkyl portion of a C7-C18 aralkyl group is replaced by a halogen atom, and examples of the same include a 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 2-chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4 group - bromobenzyl, a 2-iodobenzyl group, a 3-iodobenzyl group, a 4-iodobenzyl group, a 2,4-difluorobenzyl group, a 2,5-dichlorobenzyl group, a 2,4,6-trifluorobenzyl group, a group 2 , 3,4-trichlorobenzyl, a pentafluorobenzyl group, a 2-bromo-3-fluorobenzyl group, a 2-chloro-4-fluorobenzyl group, a 2- (4-bromophenyl) ethyl group, a 3- (4-iodophenyl group) ) propyl, a 4- (4-fluorophenyl) butyl group, a 6-fluoro-1-pyrenylmethyl group, and a 1,1-difluoro-1-phenylmethyl group.

[00131] Examples of the C7-C18 arylalkoxy group include a benzyloxy group, a phenethyloxy group, a 3-phenylpropyloxy group, a 4-phenylbutyloxy group, a 5-phenylpentyloxy group, a 6-phenylhexyloxy group, a naphthylmethyloxy group, a naphthyl group , a naphthylpropyloxy group, a naphthylbutyloxy group, an antrylmethyloxy group, an antrylethyloxy group, an antrylpropyloxy group, and an antrylbutyloxy group.

[00132] The C7-C18 haloarylalkoxy group represents a group in which at least one hydrogen atom of the aryl portion and / or the alkoxy portion of a C7-C18 arylalkoxy group is replaced by a halogen atom, and examples thereof include a 4-fluorobenzyloxy group, 2-chlorobenzyloxy group, 3-bromobenzyloxy group, 4-iodobenzyloxy group, 2,4-difluorobenzyloxy group, 2,5-dichlorobenzyloxy group, 3,4,5-trifluorobenzyloxy group, 3,4 2,3,4-trichlorobenzyloxy group, a pentafluorobenzyloxy group, a 4-bromo-2-fluorobenzyloxy group, a 2-chloro-3-fluorobenzyloxy group, a 6-chloro-2-fluorobenzyloxy group, a 2- (4- fluorophenyl) ethyloxy, a 2- (3- chlorophenyl) ethyloxy group, a 2- (2-bromophenyl) ethyloxy group, a 3- (4-iodophenyl) propyloxy group, a 3- (3-fluorophenyl) propyloxy group, a group 3- (2-chlorophenyl) propyloxy, a 4-fluoro-1-naphthylmethyloxy group, a 1- chloro-2-naphthylmethyloxy group, a 2- (5-fluoro-1-naphthyl) ethyloxy group, a 3- (6 -chloro-2-naphthyl) propyloxy, a 4- (5 -bromo-1-naphthyl) butyloxy, a 3-fluoro-1-acenaphthylmethyloxy group, a 9-fluoro-1-phenanthrylmethyloxy group, a 10-fluoro-9-antrylmethyloxy group, a 6-fluoro-1-pyrenylmethyloxy group, and a 1,1-difluoro-1-phenylmethyloxy group.

[00133] The C3-C12 trialkylsilyl group represents a group in which three hydrogen atoms in a silyl group, each of which can independently be replaced by an alkyl group, and examples of the same include a trimethylsilyl group, a tert-butyldimethylsilyl group, a triethylsilyl group, an isopropyl dimethylsilyl group, a triisopropylsilyl group, a tri (tert-butyl) silyl group, and a tributylsilyl group.

[00134] The C5-C14 trialkylsilylethynyl group represents an ethyl group to be attached to a C3-C12 trialkylsilyl group, and examples thereof include a trimethylsilylethynyl group, a tert-butyldimethylsilylethinyl group, a triethylsilylethynyl group, an isopropylthimethylethylethyl group , a triisopropylsilylethynyl group, a tri (tert-butyl) silylethynyl group, and a tributylsilylethynyl group.

[00135] The aminosulfonyl group optionally having a C1-C6 alkyl group and / or a C6-C12 aryl group represents an aminesufonyl group in which one or two hydrogen atoms in nitrogen, each of which can independently be replaced by a C1 group - C6 alkyl and / or a C6-C12 aryl group, and examples thereof include an aminosulfonyl group, an N-methylaminosulfonyl group, an N-ethylaminosulfonyl group, an N-propylaminosulfonyl group, an N-isopropylaminosulfonyl group, an N- butylaminosulfonyl, an N, N-dimethylaminosulfonyl group, an N, N-diethylaminosulfonyl group, an N, N-dipropylaminosulfonyl group, an N, N-diisopropylaminosulfonyl group, an N-ethyl-N-methylaminosulfonyl group, an N-propyl- group N-methylaminosulfonyl, an N-phenylaminosulfonyl group, an N, N-diphenylaminosulfonyl group, an N-methyl-N-phenylaminosulfonyl group, an N-ethyl-N-phenylaminosulfonyl group, an N-propyl-N-phenylaminosulfonyl group, a group N- (1-naphthyl) aminosulfonyl, a group N- (1-naphthyl) N-methylaminosulfonyl, an N- (2-naphthyl) aminosulfonyl group, and an N- (2-naphthyl) N-methylaminosulfonyl group.

[00136] The C1-C6 alkylsulfonyl group can be either straight or branched, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a sec-butylsulfonyl group , a pentylsulfonyl group, an isoamylsulfonyl group, a neopentylsulfonyl group, a 2-pentylsulfonyl group, a 3-pentylsulfonyl group, a 2-methylbutylsulfonyl group, a hexylsulfonyl group, an isohexylsulfonyl group, a 3-methylpentylsulfonyl group, and a 4- group methylpentylsulfonyl.

[00137] The C1-C6 haloalkylsulfonyl group represents a group in which at least one hydrogen atom of a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms is replaced by a halogen atom, and examples of the same include triflu - oromethylsulfonyl, a trichloromethylsulfonyl group, a tribromomethylsulfonyl group, a triiodomethylsulfonyl group, a pentafluoroethylsulfonyl group, a pentachlorethylsulfonyl group, a pentabromoethylsulfonyl group, a pentaiodoethylsulfonyl group, a 2,2,2- tricl group , 2,2-trifluoroethylsulfonyl, a heptafluoropropylsulfonyl group, a heptachloropropylsulfonyl group, a 3,3,3-trifluoropropylsulfonyl group, and a 3,3,3-trichloropropylsulfonyl group.

[00138] Examples of the C6-C16 arylsulfonyl group include a phenylsulfonyl group, a naphthylsulfonyl group, an acenaphthylsulfonyl group, a phenanthylsulfonyl group, an anthrylsulfonyl group, and a 1-pyrenylsulfonyl group.

[00139] The C6-C16 haloarylsulfonyl group represents a group in which at least one hydrogen atom of a C6-C16 arylsulfonyl group is replaced by a halogen atom, and examples of the same include a 2-fluorophenylsulfonyl group 3-fluorophenylsulfonyl, a 4-fluorophenylsulfonyl group, a 2-chlorophenylsulfonyl group, a 3-chlorophenylsulfonyl group, a 4-chlorophenylsulfonyl group, a 2-bromophenylsulfonyl group, a 3-bromophenylsulfonyl group, a 4-bromophenylsulfonyl group iodophenylsulfonyl, a 2,4-difluorophenylsulfonyl group, a 2,4-dichlorophenylsulfonyl group, a 2,6-dichlorophenylsulfonyl group, a 2,4,6-trifluorophenylsulfonyl group, a 3,4,5-trifluorophenylsulfonyl group, a group 2, 4,6-trichlorophenylsulfonyl, a 3,4,5-trichlorophenylsulfonyl group, a pentafluorophenylsulfonyl group, a 3-bromo-4-fluorophenylsulfonyl group, a 4-bromo-3-fluorophenylsulfonyl group, a 4-bromo-2-fluorophenylsulfonyl group, a 2-bromo-6-fluorophenylsulfonyl group, a 2-chloro-4-fluorophenylsulfonyl group, a 2-chloro-6-fluorophenylsulfonyl group, a 2-fluoro-1-naphthylsulfonyl group, and a 6-fluoro-1-pyrenylsulfonyl group.

[00140] The C1-C6 alkylsulfinyl group can be either straight or branched, and examples thereof include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, a sec-butylsulfinyl group , a pentylsulfinyl group, an isoamylsulfinyl group, a neopentylsulfinyl group, a 2-pentylsulfinyl group, a 3-pentylsulfinyl group, a 2-methylbutylsulfinyl group, a hexylsulfinyl group, an isoexylsulfinyl group, a 3-methylpentylsulfinyl group, and a 4- group methylpentylsulfinyl.

[00141] The C1-C6 haloalkylsulfinyl group represents a group in which at least one hydrogen atom of a C1-C6 alkylsulfinyl group is replaced by a halogen atom, and examples thereof include trifluoromethylsulfinyl, a trichloromethylsulfinyl group, a tribromomethylsulfinyl group , a triiodomethylsulfinyl group, a pentafluoroethylsulfinyl group, a pentachlorethylsulfinyl group, a pentabromoethylsulfinyl group, a pentaiodoethylsulfinyl group, a 2,2,2-trichlorethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a 2,2,2 group -tribromoethylsulfinyl, a 2,2,2-triiodoethylsulfinyl group, a heptafluoropropylsulfinyl group, a heptachloropropylsulfinyl group, a heptabromopropylsulfinyl group, a heptaiodopropylsulfinyl group, a 3,3,3-trifluoropropylsulfinyl group, a 3,3 group 3,3,3-tribromopropylsulfinyl group, a 3,3,3-triiodopropylsulfinyl group, and a perfluorohexylsulfinyl group.

[00142] Examples of the C6-C16 arylsulfinyl group include a phenylsulfinyl group, a naphthylsulfinyl group, an acenaphthylsulfinyl group, a phenantrylsulfinyl group, an anthylsulfinyl group, and a 1-pyrenylsulfinyl group.

[00143] The C6-C16 haloarylsulfinyl group represents a group in which at least one hydrogen atom of a C6-C16 arylsulfinyl group is replaced by a halogen atom, and examples of the same include a 2-fluorophenylsulfinyl group, a group 3 - fluorophenylsulfinyl, a 4-fluorophenylsulfinyl group, a 2-chlorophenylsulfinyl group, a 3-chlorophenylsulfinyl group, a 4-chlorophenylsulfinyl group, a 2-bromophenylsulfinyl group, a 3-bromophenylsulfinyl group, a 4-bromophenylsulfinyl group, a 4-bromophenylsulfinyl group, a group , a 3-iodophenylsulfinyl group, a 4-iodophenylsulfinyl group, a 2,4-difluorophenylsulfinyl group, a 2,5-difluorophenylsulfinyl group, a 2,6-difluorophenylsulfinyl group, a 3,5-difluorophenylsulfinyl group, a 2,4 group -dichlorophenylsulfinyl, a 3,4,5-trifluorophenylsulfinyl group, a 2-bromo-5-fluorophenylsulfinyl group, a 2-chloro-4-fluorophenylsulfinyl group, a 4-chloro-2-fluorophenylsulfinyl group, a 2-fluoro-1 group -naftilsulfinyl, and a group 6 -fluoro-1-pyrenylsulfinyl.

[00144] Examples of the C3-C12 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloeptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a cycloundecyl group, and a cyclododecyl group.

[00145] The C3-C12 cycloalkyl group optionally having one or more atoms or groups selected from Group P represents a group in which hydrogen atoms of a C3-C12 cycloalkyl group are optionally substituted by one or more atoms or groups selected from Group P and, when the number of selected atoms or groups in Group P is 2 or more, each atom or group can be equal to, or different from, at least one other atom or group. Examples of the C3-C12 cycloalkyl group optionally having one or more atoms or groups selected from Group P include a cyclopropyl group, a 1-methylcyclopropyl group, a 4-bromocyclohexyl group, a 4-chlorocyclohexyl group, a 4- group fluorocyclohexyl, a 4,4-difluorocyclohexyl group, a 4-methoxycyclohexyl group, a 4-methylcyclohexyl group, and a 2,6-dichlorohexyl group.

[00146] Examples of the C3-C12 cycloalkenyl group include a 1-cyclopropenyl group, a 1-cyclobutenyl group, a 1-cyclopentenyl group, a 1-cyclohexenyl group, a 2-cyclohexenyl group, a 3-cycle group -hexenyl, a 1-cycloheptenyl group, a 1-cyclooctenyl group, a 1-cyclononenyl group, a 1-cyclodecenyl group, a 1-cycloundecenyl group, a 1-cyclododecenyl group, a 1- cyclopentadienyl group, a 1,3-cyclohexadienyl group, a 1,4-cyclohexadienyl group, and a 1,5-cyclooctadienyl group.

[00147] The C3-C12 cycloalkenyl group optionally having one or more atoms or groups selected from Group P represents the C3-C12 cycloalkenyl group in which hydrogen atoms of a C3-C12 cycloalkenyl group are optionally substituted by one or more atoms or groups selected from Group P and, when the number of selected atoms or groups in Group P is 2 or more, each atom or group can be equal to, or different from, at least one other atom or group. Examples of the C3-C12 cycloalkenyl group optionally having one or more atoms or groups selected from Group P include a 1-cyclohexenyl group, a 2-cyclohexenyl group, a 3-cyclohexenyl group, a 4-chloro-group 1-cyclohexenyl, a 4-fluoro-1-cyclohexenyl group, a 4,4-difluoro-1-cyclohexenyl group, a 4-methoxy-1-cyclohexenyl group, a 4-chloro-group 2-cyclohexenyl, a 4-fluoro-2-cyclohexenyl group, a 4-methoxy-2-cyclohexenyl group, and a 4-chloro-3-cyclohexenyl group.

[00148] Examples of the C1-C3 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group.

[00149] Examples of the C1-C3 haloalkyl group include a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a difluoromethyl group, a chlorofluoromethyl group, a dichlorofluoromethyl group, a chlorodifluoromethyl group, a trifluoromethyl group, a trichloromethyl group, tribromomethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 2-chloroethyl group, a 2,2-dichloroethyl group, a 2,2,2-trichlorethyl group , a penta-fluoroethyl group, a pentachloroethyl group, a 2-chloro-2-fluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2-fluoropropyl group, a 3-fluoropropyl group, a 2.2 group -difluoropropyl, a 2,3-difluoropropyl group, a 3,3,3-trifluoropropyl group, a heptafluoropropyl group, and a 1- (fluoromethyl) -2-fluoroethyl group.

[00150] Examples of the C1-C4 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.

[00151] The C1-C4 haloalkyl group represents a group in which at least one hydrogen atom of a C1-C4 alkyl group is replaced by a halogen atom, and examples of which include a monofluoromethyl group, a monochloromethyl group dichloromethyl, a difluoromethyl group, a trifluoromethyl group, a trichloromethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a pentafluoroethyl group, a chlorofluoromethyl group, a dichlorofluoromethyl group, a chlorodifluoromethyl group, a 2,2-difluoroethyl group, a 2-chloro-2-fluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2,2-dichloro-2-fluoroethyl group, a 2-fluoropropyl group, a group 3-fluoropropyl, a 2,2-difluoropropyl group, a 3,3,3-trifluoropropyl group, and a 4-fluorobutyl group.

[00152] Examples of the C3-C5 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group.

[00153] The C3-C5 halocycloalkyl group represents a group in which at least one hydrogen atom of a C3-C5 cycloalkyl group is replaced by a halogen atom, and examples thereof include a 2-fluorocyclopropyl group, a group 2, 2- difluorocyclopropyl, a 2-chloro-2-fluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, a 2,2-dibromocyclopropyl group, a 2,2,3,3-tetrafluorocyclobutyl group, a 2-chlorocyclopentyl group, and a 3-chlorocyclopentyl group.

[00154] Examples of the C1-C4 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, and a tert-butyloxy group.

[00155] The C1-C4 haloalkoxy group represents a group in which at least one hydrogen atom of a C1-C4 alkoxy group is replaced by a halogen atom, and examples thereof include a trifluoromethoxy group, a trichloromethoxy group, a group chloromethoxy, a dichloromethoxy group, a fluoromethoxy group, a difluoromethoxy group, a chlorofluoromethoxy group, a dichlorofluoromethoxy group, a chlorodifluoromethoxy group, a pentafluoroethoxy group, a penta-chloroethoxy group, a 2,2,2-trichloro group 2,2,2-trifluoroethoxy, a 2,2,2-tribromoethoxy group, a 2,2,2-tri-iodoethoxy group, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2-chloro-2-fluoroethoxy group, a 2-chloro-2,2-difluoroethoxy group, a heptafluoropropoxy group, a hep-tachloropropoxy group, a 3,3,3- trifluoropropoxy, a 3,3,3-trichloropropoxy group, a 3,3,3-tribromopropoxy group, a 2-fluoropropoxy group, a 3-fluoropropoxy group, a 2,2-d group ifluoropropoxy, a 2,3-difluoropropoxy group, a 2-chloropropoxy group, a 3-chloropropoxy group, a 2,3-dichloropropoxy group, a 2-bromopropoxy group, a 3-bromopropoxy group, a 2,3,3- trifluoropropoxy, and a nonafluorobutoxy group.

[00156] The C2-C6 alkoxyalkyl group can be either straight or branched, and represents a group in which the total number of carbon atoms of the alkoxy portion and the alkyl portion is 2 to 6, and examples of the same include a methoxymethyl group , an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, an isobutyloxymethyl group, a sec-butyloxymethyl group, a pentyloxymethyl group, a 1-methoxyethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group , a 2-propyloxyethyl group, a 2-isopropyloxyethyl group, a 2-butyloxyethyl group, a 3-methoxypropyl group, a 3-ethoxypropyl group, a 3-propyloxypropyl group, a 3-methoxybutyl group, a 3-ethoxybutyl group, a 4-methoxybutyl group, 4-ethoxybutyl group, and 5-methoxypentyl group.

[00157] The amino group optionally having a C1-C6 alkyl group represents an amino group in which one or two hydrogen atoms in nitrogen, each independently can be replaced by a C1-C6 alkyl group, and examples of the same include a group amino, an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N, N-dimethylamino group, an N, N-diethylamino group, a group N, N-dipropylamino, an N-ethyl-N-methylamino group, and an N-propyl-N-methylamino group.

[00158] Examples of the C3-C9 trialkylsilyl group include a trimethylsilyl group, a tert-butyldimethylsilyl group, a triethylsilyl group, an isopropyl dimethylsilyl group, and a triisopropylsilyl group.

[00159] The C1-C4 alkylsulfonyl group can be either straight or branched, and examples thereof include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, and a sec- butylsulfonyl.

[00160] The C1-C4 haloalkylsulfonyl group represents a group in which at least one hydrogen atom of a C1-C4 alkylsulfonyl group is replaced by a halogen atom, and examples thereof include a trifluoromethylsulfonyl group, a trichloromethylsulfonyl group, a tribromomethylsulfonyl group, a triiodomethylsulfonyl group, a pentafluoroethylsulfonyl group, a pentachlorethylsulfonyl group, a pentabromoethylsulfonyl group, a pentaiodoethylsulfonyl group, a 2,2,2-trichloroethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, a group a heptachloropropylsulfonyl group, a 3,3,3-trifluoropropylsulfonyl group, a 3,3,3-trichloropropylsulfonyl group, and a nonafluorobutylsulfonyl group.

[00161] The C1-C4 alkylsulfinyl group can be either straight or branched, and examples thereof include methylsulfinyl, an ethylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutylsulfinyl group, and a sec group -butylsulfinyl.

[00162] The C1-C4 haloalkylsulfinyl group represents a group in which at least one hydrogen atom of a C1-C4 alkylsulfinyl group is replaced by a halogen atom, and examples thereof include trifluoromethylsulfinyl, a trichloromethylsulfinyl group, a tribromomethylsulfinyl group , a triiodomethylsulfinyl group, a pentafluoroethylsulfinyl group, a pentachloroethylsulfinyl group, a pentabromoethylsulfinyl group, a pentaiodoethylsulfinyl group, a 2,2,2-trichloroethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a hematofluoro group , a 3,3,3-trifluoropropylsulfinyl group, a 3,3,3-trichloropropylsulfinyl group, a nonafluorobutylsulfinyl group, and a nonachlorobutylsulfinyl group.

[00163] The C2-C5 alkoxyalkyl group can be either straight or branched, and represents a group in which the total number of carbon atoms of the alkoxy portion and the alkyl portion is 2 to 5, and examples of the same include methoxymethyl, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, an isobutyloxymethyl group, a sec-butyloxymethyl group, a 1-methoxyethyl group, a 2-methoxyethyl group, a 2-propyloxyethyl group, a 2- group isopropyloxyethyl, a 3-methoxypropyl group, a 3-ethoxypropyl group, a 3-methoxybutyl group, and a 4-methoxybutyl group.

The C2-C5 alkylthioalkyl group can be either straight or branched, and examples thereof include methylthiomethyl, an ethylthiomethyl group, a propylthiomethyl group, an isopropylthiomethyl group, a butylthiomethyl group, an isobutylthiomethyl group, a sec- butylthiomethyl, a 1-methylthioethyl group, a 2-methylthioethyl group, a 2-propylthioethyl group, a 2-isopropylthioethyl group, a 3-methylthiopropyl group, a 3-ethylthiopropyl group, a 3-methylthiobutyl group, and a 4-methylthiobutyl group .

[00165] Examples of the C2-C3 alkenyl group include a vinyl group, a 1-propenyl group, and a 2-propenyl group.

[00166] Examples of the C2-C3 alkynyl group include an ethyl group, a 1-propynyl group, and a 2-propynyl group.

[00167] Examples of the C3-C4 cycloalkyl group include a cyclopropyl group and a cyclobutyl group.

[00168] Examples of the C1-C3 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, and an isopropyloxy group.

[00169] The C1-C3 haloalkoxy group represents a group in which at least one hydrogen atom of a C1-C3 alkoxy group is replaced by a halogen atom, and examples thereof include a trifluoromethoxy group, a trichloromethoxy group, a group chloromethoxy, a dichloromethoxy group, a fluoromethoxy group, a difluoromethoxy group, a chlorofluoromethoxy group, a dichlorofluoromethoxy group, a chlorodifluoromethoxy group, a pentafluoroethoxy group, a penta-chloroethoxy group, a 2,2,2-trichloro group 2,2,2-trifluoroethoxy, a 2-fluoroethoxy group, a 2-chloroethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, a 2-chloro-2-fluoroethoxy group, a group 2-chloro-2,2-difluoroethoxy, a heptafluoro-propoxy group, a heptachloropropoxy group, a 3,3,3-trifluoropropoxy group, a 3,3,3-trichloropropoxy group, a 2-fluoropropoxy group, a 3- group fluoropropoxy, a 2,2-difluoropropoxy group, a 2,3-difluoropropoxy group, a 2-chloropropoxy group, a 3-chloropropox group xi, a 2,3-dichloropropoxy group, a 2-bromopropoxy group, a 3-bromopropoxy group, and a 3,3,3-trifluoropropoxy group.

[00170] Examples of the C1-C2 alkylthio group include a methylthio group and an ethylthio group.

[00171] The C1-C2 haloalkylthio group represents a group in which at least one hydrogen atom of a C1-C2 alkylthio group is replaced by a halogen atom, and examples thereof include monofluoromethylthio, a difluoromethylthio group, a trifluoro group - methylthio, a trichloromethylthio group, a tribromomethylthio group, a triiodomethylthio group, a chlorofluoromethylthio group, a pentafluoroethylthio group, a pentachlorethylthio group, a pentabromoethylthio group, a pentatodoethylthio group, a 2,2,2-trichlorethylthio group, a 2 group , 2,2-trifluoroethylthio, and a 2,2-difluoroethylthio group.

[00172] The amino group optionally having a C1-C6 haloalkyl group represents an amino group in which one or two hydrogen atoms in nitrogen, each of which can independently be replaced by a C1-C6 haloalkyl group, and examples thereof include an amino group, a 2,2,2-trifluoroethylamino group, an N, N- (2,2-ditrifluoroethyl) -amino group, an N, N- (2,2-dithricloroethyl) -amino group, and a pentafluoropropylamino group .

Examples of the C1-C4 alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, and a tert-butylthio group.

[00174] The C1-C4 haloalkylthio group represents a group in which at least one hydrogen atom of a C1-C4 alkylthio group is replaced by a halogen atom, and examples thereof include a monofluoromethylthio group, a difluoromethylthio group trifluoromethylthio, a trichloromethylthio group, a tribromomethylthio group, a triiodomethylthio group, a chlorofluoromethylthio group, a pentafluoroethylthio group, a pentachloroethylthio group, a 2,2,2-trichlorethylthio group, a 2,2,2-trifluoroethyl group, a group 2,2,2-trifluoroethylthio, and a 2,2-difluoroethylthio group.

[00175] The C2-C9 heterocyclyl group represents a 5, 6 or 7 membered saturated heterocyclic, or a 5, 6 or 7 membered heteroaryl, and the saturated heterocyclic group or the heteroaryl group has, as a ring constituent atom, one or more atoms selected from the nitrogen atom, an oxygen atom, or a sulfur atom and, when the saturated heterocyclic group or the heteroaryl group has two or more atoms selected from a nitrogen atom, an oxygen atom, or a sulfur atom, each atom can be equal to, or different from, at least one other atom.

[00176] Examples of the 5, 6, or 7-membered non-aromatic cyclic group include a pyrrolidin-1-yl group, a piperidin-1-yl group, a piperazin-1-yl group, a 4-methylpiperazin-1 group -ila, a morpholin-4-yl group, a thiomorpholin-4-yl group, or a 1-azepanyl group.

[00177] Examples of the 5-, 6-, or 7-membered C2-C9 heteroaryl group include a 1-pyrrolyl group, a 1-pyrazolyl group, a 1-imidazolyl group, a 1,2,4-triazole-1-yl group , a 2-furyl group, a 3-furyl group, a 2-thienyl group, a 3-thienyl group, a 2-pyrrolyl group, a 3-pyrrolyl group, a 3-iso-oxazolyl group, a 4-iso group -oxazolyl, a 5-iso-oxazolyl group, a 3-isothiazolyl group, a 4-isothiazolyl group, a 5-isothiazolyl group, a 3-pyrazolyl group, a 4-pyrazolyl group, a 5-pyrazolyl group, a group 2 -oxazolyl, a 4-oxazolyl group, a 5-oxazolyl group, a 2-thiazolyl group, a 4-thiazolyl group, a 5-thiazolyl group, a 2-imidazolyl group, a 4-imidazolyl group, a 2-pyridinyl group , a 3-pyridinyl group, a 4-pyridinyl group, a 3-pyridazinyl group, a 4-pyridazinyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group, a 5-pyrimidinyl group, a 2-pyrazinyl group, a 1,3,5-triazin-2-yl group, a 1,2,4-triazin-3-yl group, a 6-quin group olinyl, a 7-quinolinyl group, a 3-quinolinyl group, a 6-isoquinolinyl group, a 6-quinazolinyl group, a 6-quinoxalinyl group, a 2-purinyl group, a 5-benzofuranyl group, a benzo group [1, 3] dioxol-5-yl, and a benzoxazol-5-yl group.

[00178] The C2-C9 heterocyclyl group optionally having one or more atoms or groups selected from Group P (provided that the C2-C9 heterocyclyl group has, as a ring constituent atom, one or more atoms selected from the group consisting of one atom nitrogen, an oxygen atom, and a sulfur atom, and when the C2-C9 heterocyclyl group has two or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, each atom can be the same as, or different from at least one other group. In addition, the carbon or nitrogen atom that forms the ring of the C2-C9 heterocyclyl group is bonded to Q) represents a group in which hydrogen atoms of a C2 group - C9 heterocyclyl are optionally substituted by one or more atoms or groups selected from Group P, and represents a C2-C9 heteroaryl group optionally having one or more atoms or groups selected from Group P, and an optional non-aromatic saturated cyclic group between having one or more atoms or groups selected from Group P. When the number of atoms or groups selected from Group P is 2 or more, each atom or group can be equal to, or different from, at least one other atom or group. Examples of the C2-C9 heterocyclyl group optionally having one or more atoms or groups selected from Group P (provided that the C2-C9 heterocyclyl group has, as a ring constituent atom, one or more atoms selected from the group consisting of a nitrogen atom , an oxygen atom, and a sulfur atom, and when two or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, each atom can be equal to, or different from, hair minus one other group. In addition, the carbon or nitrogen atom that forms the ring of the C2-C9 heterocyclyl group is attached to Q) includes a 4-methylpiperazin-1-yl group, a morpholin-4-yl group, a group piperidin-1-yl, a 4-methylpiperidin-1-yl group, a 1-pyrazolyl group, a 3,4-dimethylpyrazol-1-yl group, a 4-methoxy-3,5-dimethylpyrazol-1-yl group, a 2-pyridinyl group, a 5-methoxy-2-pyridinyl group, a 5-chloro-2-pyridinyl group, a 3-pyridinyl group, a 6-methoxy-3-pyridi group nila, a 6-chloro-3-pyridinyl group, a 4-pyridinyl group, a 2-pyrazinyl group, a 5-methoxy-2-pyrazinyl group, a 5-chloro-2-pyrazinyl group, a 3-pyridazinyl group, a 6-methoxy-3-pyridazinyl group, a 6-chloro-3-pyridazinyl group, a 2-pyrimidinyl group, a 5-methoxy-2-pyrimidinyl group, a 5-pyrimidinyl group, a 2-chloro-5- group pyrimidinyl, a 5-benzofuranyl group, a 2-methylbenzofuran-5-yl group, a benzo [1,3] dioxol-5-yl group, a 2,2-dimethylbenzo [1,3] dioxol-5- group ila, a 2,2-difluorobenzo [1,3] dioxol-5-yl group, a benzoxazol-5-yl group, and a 2-methylbenzoxazol-5-yl group.

[00179] Examples of the appearance of the present compound include compounds in which the substituent in formula (1) is shown below:

[00180] a compound in which A is an aryl group;

[00181] a compound in which A is a pyridyl group;

[00182] a compound in which A is a haloaryl group;

[00183] a compound in which A is an aryl group having a C1-C3 alkyl group;

[00184] a compound in which A is an aryl group having a C1-C3 haloalkyl group;

[00185] a compound in which A is an aryl group having a C1-C3 alkoxy group;

[00186] a compound in which A is an aryl group having a C1-C3 haloalkoxy group;

[00187] a compound in which A is a pyridyl group having a C1-C3 alkoxy group;

[00188] a compound in which A is a 4-chlorophenyl group;

[00189] a compound in which A is a 4-fluorophenyl group;

[00190] a compound in which A is a 4-bromophenyl group;

[00191] a compound in which A is a 4-methoxyphenyl group;

[00192] a compound in which A is a 4-ethoxyphenyl group;

[00193] a compound in which A is a 4-isopropyloxyphenyl group;

[00194] a compound in which A is a 4-trifluoromethoxyphenyl group;

[00195] a compound in which R1 is a hydrogen atom;

[00196] a compound in which R2 is a hydrogen atom;

[00197] a compound in which R4 is a hydrogen atom;

[00198] a compound in which R5 is a hydrogen atom;

[00199] a compound in which R6 is a hydrogen atom;

[00200] a compound in which R3 is a C1-C3 alkyl group;

[00201] a compound in which R3 is a C3-C4 cycloalkyl group;

[00202] a compound in which R3 is a halogen atom;

[00203] a compound in which R3 is a C1-C3 haloalkyl group;

[00204] a compound in which R3 is a C2-C3 alkenyl group;

[00205] a compound in which R3 is a C1-C3 alkoxy group;

[00206] a compound in which R3 is a C2-C3 alkynyl group;

[00207] a compound in which R3 is a C1-C3 haloalkoxy group;

[00208] a compound in which R3 is a C1-C3 alkyl group, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C2-C3 alkynyl group, or a C1-C3 haloalkoxy group;

[00209] a compound in which R3 is a methyl group;

[00210] a compound in which R3 is an ethyl group;

[00211] a compound in which R3 is a propyl group;

[00212] a compound in which R3 is a cyclopropyl group;

[00213] a compound in which R3 is a trifluoromethyl group;

[00214] a compound in which R3 is a difluoromethyl group;

[00215] a compound in which R3 is a vinyl group;

[00216] a compound in which R3 is a 2-propenyl group;

[00217] a compound in which R3 is a chlorine atom;

[00218] a compound in which R3 is a bromine atom;

[00219] a compound in which R3 is an iodine atom;

[00220] a compound in which R3 is a fluorine atom;

[00221] a compound in which R3 is a methoxy group;

[00222] a compound in which R3 is an ethoxy group;

[00223] a compound in which R7 is a methyl group;

[00224] a compound in which X is an oxygen atom; and

[00225] a compound in which X is a sulfur atom.

[00226] A tetrazolinone compound in which A is a formula (2).

[Aspect 1]

[00227] A tetrazolinone compound in which A is a formula (2), R37, R38, R39, R40, and R41 each independently represents a halogen atom, a hydrogen atom, a C1-C6 alkyl group, a C1 group -C6 haloalkyl, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a C3-C6 cycloalkyl group, a C2-C6 alkylcarbonyloxy group, a formyl group, a C2-C6 group alkoxycarbonyl, a C2-C6 alkylcarbonyl group, a nitro group, a cyano group, a hydroxyl group, a C6-C16 aryloxy group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylsulfinyl group, an aminosulfonyl group optionally having a C1 group -C6 alkyl and / or a C6-C12 aryl group, or an amino group optionally having a C1-C6 alkyl group; R1, R2, R4, R5, and R6 are hydrogen atoms; R7 is a methyl group; and X is an oxygen atom.

[00228] A tetrazolinone compound in which R3 is a C1- C3 alkyl group in [Aspect 1],

[00229] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group in [Aspect 1],

[00230] A tetrazolinone compound in which R3 is a halogen atom in [Aspect 1],

[00231] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group in [Aspect 1].

[00232] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group in [Aspect 1],

[00233] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group in [Aspect 1].

[00234] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group in [Aspect 1].

[00235] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group in [Aspect 1].

[00236] A tetrazolinone compound in which R3 is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a methyl group in [Aspect 1],

[00237] A tetrazolinone compound in which R3 is a C1- C3 alkyl group, a C1-C3 haloalkyl group, a C3-C4 cycloalkyl group, a C2-C3 alkenyl group, or a C2-C3 alkynyl group in [Aspect] 1],

[00238] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group or a C1-C3 haloalkoxy group in [Aspect 1],

[00239] A tetrazolinone compound in which R3 is a methyl group in [Aspect 1],

[00240] A tetrazolinone compound in which R3 is an ethyl group in [Aspect 1],

[00241] A tetrazolinone compound in which R3 is a cyclopropyl group in [Aspect 1],

[00242] A tetrazolinone compound in which R3 is a chlorine atom in [Aspect 1],

[00243] A tetrazolinone compound in which R3 is a bromine atom in [Aspect 1],

[00244] A tetrazolinone compound in which R3 is a methoxy group in [Aspect 1],

[00245] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q1 in [Aspect 1],

[00246] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q1 in [Aspect 1],

[00247] A tetrazolinone compound in which R3 is a halogen atom and Q is Q1 in [Aspect 1],

[00248] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q1 in [Aspect 1],

[00249] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q1 in [Aspect 1],

[00250] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q1 in [Aspect 1],

[00251] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q1 in [Aspect 1],

[00252] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q1 in [Aspect 1],

[00253] A tetrazolinone compound in which R3 is a methyl group and Q is Q1 in [Aspect 1].

[00254] A tetrazolinone compound in which R3 is an ethyl group and Q is Q1 in [Aspect 1],

[00255] A tetrazolinone compound in which R3 is a cyclopropyl group, and Q is Q1 in [Aspect 1],

[00256] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q1 in [Aspect 1],

[00257] A tetrazolinone compound in which R3 is a bromine atom and Q is Q1 in [Aspect 1],

[00258] A tetrazolinone compound in which R3 is a methoxy group and Q is Q1 in [Aspect 1].

[00259] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q2 in [Aspect 1],

[00260] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q2 in [Aspect 1],

[00261] A tetrazolinone compound in which R3 is a halogen atom and Q is Q2 in [Aspect 1],

[00262] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q2 in [Aspect 1],

[00263] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q2 in [Aspect 1],

[00264] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q2 in [Aspect 1],

[00265] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q2 in [Aspect 1],

[00266] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q2 in [Aspect 1],

[00267] A tetrazolinone compound in which R3 is a methyl group and Q is Q2 in [Aspect 1].

[00268] A tetrazolinone compound in which R3 is an ethyl group and Q is Q2 in [Aspect 1],

[00269] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q2 in [Aspect 1],

[00270] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q2 in [Aspect 1],

[00271] A tetrazolinone compound in which R3 is a bromine atom and Q is Q2 in [Aspect 1],

[00272] A tetrazolinone compound in which R3 is a methoxy group and Q is Q2 in [Aspect 1].

[00273] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q3 in [Aspect 1],

[00274] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q3 in [Aspect 1],

[00275] A tetrazolinone compound in which R3 is a halogen atom and Q is Q3 in [Aspect 1],

[00276] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q3 in [Aspect 1],

[00277] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q3 in [Aspect 1],

[00278] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q3 in [Aspect 1],

[00279] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q3 in [Aspect 1],

[00280] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q3 in [Aspect 1],

[00281] A tetrazolinone compound in which R3 is a methyl group and Q is Q3 in [Aspect 1].

[00282] A tetrazolinone compound in which R3 is an ethyl group and Q is Q3 in [Aspect 1],

[00283] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q3 in [Aspect 1],

[00284] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q3 in [Aspect 1],

[00285] A tetrazolinone compound in which R3 is a bromine atom and Q is Q3 in [Aspect 1],

[00286] A tetrazolinone compound in which R3 is a methoxy group and Q is Q3 in [Aspect 1].

[00287] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q4 in [Aspect 1]

[00288] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q4 in [Aspect 1],

[00289] A tetrazolinone compound in which R3 is a halogen atom and Q is Q4 in [Aspect 1],

[00290] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q4 in [Aspect 1],

[00291] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q4 in [Aspect 1],

[00292] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q4 in [Aspect 1],

[00293] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q4 in [Aspect 1],

[00294] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q4 in [Aspect 1],

[00295] A tetrazolinone compound in which R3 is a methyl group and Q is Q4 in [Aspect 1],

[00296] A tetrazolinone compound in which R3 is an ethyl group and Q is Q4 in [Aspect 1].

[00297] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q4 in [Aspect 1],

[00298] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q4 in [Aspect 1],

[00299] A tetrazolinone compound in which R3 is a bromine atom and Q is Q4 in [Aspect 1],

[00300] A tetrazolinone compound in which R3 is a methoxy group and Q is Q4 in [Aspect 1].

[00301] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q5 in [Aspect 1],

[00302] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q5 in [Aspect 1],

[00303] A tetrazolinone compound in which R3 is a halogen atom, and Q is Q5 in [Aspect 1],

[00304] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q5 in [Aspect 1],

[00305] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q5 in [Aspect 1],

[00306] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q5 in [Aspect 1].

[00307] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q5 in [Aspect 1].

[00308] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q5 in [Aspect 1],

[00309] A tetrazolinone compound in which R3 is a methyl group and Q is Q5 in [Aspect 1],

[00310] A tetrazolinone compound in which R3 is an ethyl group and Q is Q5 in [Aspect 1],

[00311] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q5 in [Aspect 1].

[00312] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q5 in [Aspect 1],

[00313] A tetrazolinone compound in which R3 is a bromine atom and Q is Q5 in [Aspect 1],

[00314] A tetrazolinone compound in which R3 is a methoxy group and Q is Q5 in [Aspect 1],

[00315] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q6 in [Aspect 1],

[00316] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q6 in [Aspect 1],

[00317] A tetrazolinone compound in which R3 is a halogen atom and Q is Q6 in [Aspect 1],

[00318] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q6 in [Aspect 1],

[00319] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q6 in [Aspect 1],

[00320] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q6 in [Aspect 1],

[00321] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q6 in [Aspect 1],

[00322] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q6 in [Aspect 1],

[00323] A tetrazolinone compound in which R3 is a methyl group and Q is Q6 in [Aspect 1].

[00324] A tetrazolinone compound in which R3 is an ethyl group and Q is Q6 in [Aspect 1],

[00325] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q6 in [Aspect 1],

[00326] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q6 in [Aspect 1],

[00327] A tetrazolinone compound in which R3 is a bromine atom and Q is Q6 in [Aspect 1],

[00328] A tetrazolinone compound in which R3 is a methoxy group and Q is Q6 in [Aspect 1].

[00329] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q7 in [Aspect 1],

[00330] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q7 in [Aspect 1],

[00331] A tetrazolinone compound in which R3 is a halogen atom and Q is Q7 in [Aspect 1],

[00332] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q7 in [Aspect 1],

[00333] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q7 in [Aspect 1],

[00334] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q7 in [Aspect 1],

[00335] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q7 in [Aspect 1],

[00336] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q7 in [Aspect 1],

[00337] A tetrazolinone compound in which R3 is a methyl group and Q is Q7 in [Aspect 1].

[00338] A tetrazolinone compound in which R3 is an ethyl group and Q is Q7 in [Aspect 1],

[00339] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q7 in [Aspect 1],

[00340] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q7 in [Aspect 1],

[00341] A tetrazolinone compound in which R3 is a bromine atom and Q is Q7 in [Aspect 1],

[00342] A tetrazolinone compound in which R3 is a methoxy group and Q is Q7 in [Aspect 1].

[00343] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q8 in [Aspect 1],

[00344] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q8 in [Aspect 1],

[00345] A tetrazolinone compound in which R3 is a halogen atom and Q is Q8 in [Aspect 1],

[00346] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q8 in [Aspect 1],

[00347] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q8 in [Aspect 1],

[00348] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q8 in [Aspect 1],

[00349] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q8 in [Aspect 1],

[00350] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q8 in [Aspect 1],

[00351] A tetrazolinone compound in which R3 is a methyl group and Q is Q8 in [Aspect 1].

[00352] A tetrazolinone compound in which R3 is an ethyl group and Q is Q8 in [Aspect 1],

[00353] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q8 in [Aspect 1],

[00354] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q8 in [Aspect 1],

[00355] A tetrazolinone compound in which R3 is a bromine atom and Q is Q8 in [Aspect 1],

[00356] A tetrazolinone compound in which R3 is a methoxy group and Q is Q8 in [Aspect 1].

[00357] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q9 in [Aspect 1],

[00358] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q9 in [Aspect 1],

[00359] A tetrazolinone compound in which R3 is a halogen atom and Q is Q9 in [Aspect 1],

[00360] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q9 in [Aspect 1],

[00361] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q9 in [Aspect 1],

[00362] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q9 in [Aspect 1],

[00363] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q9 in [Aspect 1],

[00364] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q9 in [Aspect 1],

[00365] A tetrazolinone compound in which R3 is a methyl group and Q is Q9 in [Aspect 1],

[00366] A tetrazolinone compound in which R3 is an ethyl group and Q is Q9 in [Aspect 1],

[00367] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q9 in [Aspect 1].

[00368] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q9 in [Aspect 1].

[00369] A tetrazolinone compound in which R3 is a bromine atom and Q is Q9 in [Aspect 1].

[00370] A tetrazolinone compound in which R3 is a methoxy group and Q is Q9 in [Aspect 1].

[00371] A tetrazolinone compound in which R3 is a CI-03 alkyl group and Q is Q10 in [Aspect 1],

[00372] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q10 in [Aspect 1],

[00373] A tetrazolinone compound in which R3 is a halogen atom and Q is Q10 in [Aspect 1],

[00374] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q10 in [Aspect 1],

[00375] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q10 in [Aspect 1],

[00376] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q10 in [Aspect 1],

[00377] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q10 in [Aspect 1],

[00378] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q10 in [Aspect 1],

[00379] A tetrazolinone compound in which R3 is a methyl group and Q is Q10 in [Aspect 1].

[00380] A tetrazolinone compound in which R3 is an ethyl group and Q is Q10 in [Aspect 1],

[00381] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q10 in [Aspect 1].

[00382] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q10 in [Aspect 1].

[00383] A tetrazolinone compound in which R3 is a bromine atom and Q is Q10 in [Aspect 1],

[00384] A tetrazolinone compound in which R3 is a methoxy group and Q is Q10 in [Aspect 1].

[00385] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q11 in [Aspect 1],

[00386] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q11 in [Aspect 1],

[00387] A tetrazolinone compound in which R3 is a halogen atom and Q is Q11 in [Aspect 1],

[00388] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q11 in [Aspect 1],

[00389] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q11 in [Aspect 1],

[00390] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q11 in [Aspect 1],

[00391] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q11 in [Aspect 1],

[00392] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q11 in [Aspect 1],

[00393] A tetrazolinone compound in which R3 is a methyl group and Q is Q11 in [Aspect 1].

[00394] A tetrazolinone compound in which R3 is an ethyl group and Q is Q11 in [Aspect 1].

[00395] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q11 in [Aspect 1],

[00396] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q11 in [Aspect 1],

[00397] A tetrazolinone compound in which R3 is a bromine atom and Q is Q11 in [Aspect 1],

[00398] A tetrazolinone compound in which R3 is a methoxy group and Q is Q11 in [Aspect 1],

[00399] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q12 in [Aspect 1],

[00400] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q12 in [Aspect 1],

[00401] A tetrazolinone compound in which R3 is a halogen atom and Q is Q12 in [Aspect 1],

[00402] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q12 in [Aspect 1],

[00403] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q12 in [Aspect 1],

[00404] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q12 in [Aspect 1],

[00405] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q12 in [Aspect 1],

[00406] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q12 in [Aspect 1],

[00407] A tetrazolinone compound in which R3 is a methyl group and Q is Q12 in [Aspect 1],

[00408] A tetrazolinone compound in which R3 is an ethyl group and Q is Q12 in [Aspect 1],

[00409] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q12 in [Aspect 1],

[00410] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q12 in [Aspect 1],

[00411] A tetrazolinone compound in which R3 is a bromine atom and Q is Q12 in [Aspect 1],

[00412] A tetrazolinone compound in which R3 is a methoxy group and Q is Q12 in [Aspect 1],

[Aspect 2]

[00413] A tetrazolinone compound in which A is of formula (2), R37 represents a halogen atom, a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, or a C1-C3 haloalkoxy group; R38, R39, R40, and R41 each independently represent a hydrogen atom or a halogen atom; R1, R2, R4, R5, and R6 are hydrogen atoms; R7 is a methyl group; and X is an oxygen atom.

[00414] A tetrazolinone compound in which R3 is a C1- C3 alkyl group in [Aspect 2],

[00415] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group in [Aspect 2],

[00416] A tetrazolinone compound in which R3 is a halogen atom in [Aspect 2],

[00417] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group in [Aspect 2],

[00418] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group in [Aspect 2].

[00419] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group in [Aspect 2].

[00420] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group in [Aspect 2],

[00421] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group in [Aspect 2].

[00422] A tetrazolinone compound in which R3 is a methyl group in [Aspect 2].

[00423] A tetrazolinone compound in which R3 is an ethyl group in [Aspect 2].

[00424] A tetrazolinone compound in which R3 is a cyclopropyl group in [Aspect 2],

[00425] A tetrazolinone compound in which R3 is a chlorine atom in [Aspect 2],

[00426] A tetrazolinone compound in which R3 is a bromine atom in [Aspect 2],

[00427] A tetrazolinone compound in which R3 is a methoxy group in [Aspect 2],

[00428] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q1 in [Aspect 2],

[00429] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q1 in [Aspect 2],

[00430] A tetrazolinone compound in which R3 is a halogen atom and Q is Q1 in [Aspect 2],

[00431] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q1 in [Aspect 2],

[00432] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q1 in [Aspect 2],

[00433] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q1 in [Aspect 2],

[00434] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q1 in [Aspect 2],

[00435] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q1 in [Aspect 2],

[00436] A tetrazolinone compound in which R3 is a methyl group and Q is Q1 in [Aspect 2].

[00437] A tetrazolinone compound in which R3 is an ethyl group and Q is Q1 in [Aspect 2],

[00438] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q1 in [Aspect 2],

[00439] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q1 in [Aspect 2],

[00440] A tetrazolinone compound in which R3 is a bromine atom and Q is Q1 in [Aspect 2],

[00441] A tetrazolinone compound in which R3 is a methoxy group and Q is Q1 in [Aspect 2],

[00442] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q2 in [Aspect 2],

[00443] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q2 in [Aspect 2],

[00444] A tetrazolinone compound in which R3 is a halogen atom and Q is Q2 in [Aspect 2],

[00445] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q2 in [Aspect 2],

[00446] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q2 in [Aspect 2],

[00447] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q2 in [Aspect 2],

[00448] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q2 in [Aspect 2],

[00449] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q2 in [Aspect 2],

[00450] A tetrazolinone compound in which R3 is a methyl group and Q is Q2 in [Aspect 2].

[00451] A tetrazolinone compound in which R3 is an ethyl group and Q is Q2 in [Aspect 2],

[00452] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q2 in [Aspect 2],

[00453] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q2 in [Aspect 2],

[00454] A tetrazolinone compound in which R3 is a bromine atom and Q is Q2 in [Aspect 2],

[00455] A tetrazolinone compound in which R3 is a methoxy group and Q is Q2 in [Aspect 2],

[00456] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q3 in [Aspect 2].

[00457] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q3 in [Aspect 2],

[00458] A tetrazolinone compound in which R3 is a halogen atom and Q is Q3 in [Aspect 2],

[00459] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q3 in [Aspect 2],

[00460] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q3 in [Aspect 2],

[00461] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q3 in [Aspect 2],

[00462] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q3 in [Aspect 2],

[00463] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q3 in [Aspect 2],

[00464] A tetrazolinone compound in which R3 is a methyl group and Q is Q3 in [Aspect 2].

[00465] A tetrazolinone compound in which R3 is an ethyl group and Q is Q3 in [Aspect 2],

[00466] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q3 in [Aspect 2],

[00467] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q3 in [Aspect 2],

[00468] A tetrazolinone compound in which R3 is a bromine atom and Q is Q3 in [Aspect 2],

[00469] A tetrazolinone compound in which R3 is a methoxy group and Q is Q3 in [Aspect 2].

[00470] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q4 in [Aspect 2],

[00471] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q4 in [Aspect 2],

[00472] A tetrazolinone compound in which R3 is a halogen atom and Q is Q4 in [Aspect 2],

[00473] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q4 in [Aspect 2],

[00474] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q4 in [Aspect 2],

[00475] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q4 in [Aspect 2],

[00476] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q4 in [Aspect 2],

[00477] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q4 in [Aspect 2],

[00478] A tetrazolinone compound in which R3 is a methyl group and Q is Q4 in [Aspect 2].

[00479] A tetrazolinone compound in which R3 is an ethyl group and Q is Q4 in [Aspect 2],

[00480] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q4 in [Aspect 2],

[00481] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q4 in [Aspect 2],

[00482] A tetrazolinone compound in which R3 is a bromine atom and Q is Q4 in [Aspect 2],

[00483] A tetrazolinone compound in which R3 is a methoxy group and Q is Q4 in [Aspect 2],

[00484] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q5 in [Aspect 2],

[00485] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q5 in [Aspect 2],

[00486] A tetrazolinone compound in which R3 is a halogen atom and Q is Q5 in [Aspect 2],

[00487] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q5 in [Aspect 2],

[00488] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q5 in [Aspect 2],

[00489] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q5 in [Aspect 2],

[00490] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q5 in [Aspect 2],

[00491] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q5 in [Aspect 2],

[00492] A tetrazolinone compound in which R3 is a methyl group and Q is Q5 in [Aspect 2].

[00493] A tetrazolinone compound in which R3 is an ethyl group and Q is Q5 in [Aspect 2],

[00494] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q5 in [Aspect 2],

[00495] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q5 in [Aspect 2],

[00496] A tetrazolinone compound in which R3 is a bromine atom and Q is Q5 in [Aspect 2],

[00497] A tetrazolinone compound in which R3 is a methoxy group and Q is Q5 in [Aspect 2],

[00498] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q6 in [Aspect 2],

[00499] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q6 in [Aspect 2],

[00500] A tetrazolinone compound in which R3 is a halogen atom and Q is Q6 in [Aspect 2],

[00501] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q6 in [Aspect 2],

[00502] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q6 in [Aspect 2],

[00503] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q6 in [Aspect 2],

[00504] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q6 in [Aspect 2],

[00505] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q6 in [Aspect 2],

[00506] A tetrazolinone compound in which R3 is a methyl group and Q is Q6 in [Aspect 2].

[00507] A tetrazolinone compound in which R3 is an ethyl group and Q is Q6 in [Aspect 2],

[00508] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q6 in [Aspect 2],

[00509] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q6 in [Aspect 2],

[00510] A tetrazolinone compound in which R3 is a bromine atom and Q is Q6 in [Aspect 2],

[00511] A tetrazolinone compound in which R3 is a methoxy group and Q is Q6 in [Aspect 2],

[00512] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q7 in [Aspect 2],

[00513] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q7 in [Aspect 2],

[00514] A tetrazolinone compound in which R3 is a halogen atom, and Q is Q7 in [Aspect 2],

[00515] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q7 in [Aspect 2],

[00516] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q7 in [Aspect 2],

[00517] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q7 in [Aspect 2],

[00518] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q7 in [Aspect 2],

[00519] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q7 in [Aspect 2],

[00520] A tetrazolinone compound in which R3 is a methyl group and Q is Q7 in [Aspect 2].

[00521] A tetrazolinone compound in which R3 is an ethyl group and Q is Q7 in [Aspect 2],

[00522] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q7 in [Aspect 2],

[00523] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q7 in [Aspect 2],

[00524] A tetrazolinone compound in which R3 is a bromine atom and Q is Q7 in [Aspect 2],

[00525] A tetrazolinone compound in which R3 is a methoxy group and Q is Q7 in [Aspect 2],

[00526] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q8 in [Aspect 2],

[00527] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q8 in [Aspect 2],

[00528] A tetrazolinone compound in which R3 is a halogen atom and Q is Q8 in [Aspect 2],

[00529] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q8 in [Aspect 2],

[00530] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q8 in [Aspect 2],

[00531] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q8 in [Aspect 2],

[00532] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q8 in [Aspect 2],

[00533] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q8 in [Aspect 2],

[00534] A tetrazolinone compound in which R3 is a methyl group and Q is Q8 in [Aspect 2].

[00535] A tetrazolinone compound in which R3 is an ethyl group and Q is Q8 in [Aspect 2],

[00536] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q8 in [Aspect 2],

[00537] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q8 in [Aspect 2],

[00538] A tetrazolinone compound in which R3 is a bromine atom and Q is Q8 in [Aspect 2],

[00539] A tetrazolinone compound in which R3 is a methoxy group and Q is Q8 in [Aspect 2],

[00540] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q9 in [Aspect 2],

[00541] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q9 in [Aspect 2],

[00542] A tetrazolinone compound in which R3 is a halogen atom and Q is Q9 in [Aspect 2],

[00543] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q9 in [Aspect 2],

[00544] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q9 in [Aspect 2],

[00545] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q9 in [Aspect 2],

[00546] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q9 in [Aspect 2],

[00547] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q9 in [Aspect 2],

[00548] A tetrazolinone compound in which R3 is a methyl group and Q is Q9 in [Aspect 2].

[00549] A tetrazolinone compound in which R3 is an ethyl group and Q is Q9 in [Aspect 2],

[00550] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q9 in [Aspect 2],

[00551] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q9 in [Aspect 2],

[00552] A tetrazolinone compound in which R3 is a bromine atom and Q is Q9 in [Aspect 2],

[00553] A tetrazolinone compound in which R3 is a methoxy group and Q is Q9 in [Aspect 2],

[00554] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q10 in [Aspect 2],

[00555] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q10 in [Aspect 2],

[00556] A tetrazolinone compound in which R3 is a halogen atom and Q is Q10 in [Aspect 2],

[00557] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q10 in [Aspect 2],

[00558] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q10 in [Aspect 2],

[00559] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q10 in [Aspect 2],

[00560] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q10 in [Aspect 2],

[00561] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q10 in [Aspect 2],

[00562] A tetrazolinone compound in which R3 is a methyl group and Q is Q10 in [Aspect 2],

[00563] A tetrazolinone compound in which R3 is an ethyl group and Q is Q10 in [Aspect 2],

[00564] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q10 in [Aspect 2],

[00565] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q10 in [Aspect 2],

[00566] A tetrazolinone compound in which R3 is a bromine atom and Q is Q10 in [Aspect 2],

[00567] A tetrazolinone compound in which R3 is a methoxy group and Q is Q10 in [Aspect 2],

[00568] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q11 in [Aspect 2],

[00569] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q11 in [Aspect 2],

[00570] A tetrazolinone compound in which R3 is a halogen atom and Q is Q11 in [Aspect 2],

[00571] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q11 in [Aspect 2],

[00572] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q11 in [Aspect 2],

[00573] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q11 in [Aspect 2],

[00574] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q11 in [Aspect 2],

[00575] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q11 in [Aspect 2],

[00576] A tetrazolinone compound in which R3 is a methyl group and Q is Q11 in [Aspect 2],

[00577] A tetrazolinone compound in which R3 is an ethyl group and Q is Q11 in [Aspect 2].

[00578] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q11 in [Aspect 2].

[00579] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q11 in [Aspect 2],

[00580] A tetrazolinone compound in which R3 is a bromine atom and Q is Q11 in [Aspect 2],

[00581] A tetrazolinone compound in which R3 is a methoxy group and Q is Q11 in [Aspect 2],

[00582] A tetrazolinone compound in which R3 is a C1- C3 alkyl group and Q is Q12 in [Aspect 2],

[00583] A tetrazolinone compound in which R3 is a C3-C4 cycloalkyl group and Q is Q12 in [Aspect 2],

[00584] A tetrazolinone compound in which R3 is a halogen atom and Q is Q12 in [Aspect 2],

[00585] A tetrazolinone compound in which R3 is a C1- C3 haloalkyl group and Q is Q12 in [Aspect 2],

[00586] A tetrazolinone compound in which R3 is a C2-C3 alkenyl group and Q is Q12 in [Aspect 2],

[00587] A tetrazolinone compound in which R3 is a C1- C3 alkoxy group and Q is Q12 in [Aspect 2],

[00588] A tetrazolinone compound in which R3 is a C2-C3 alkynyl group and Q is Q12 in [Aspect 2],

[00589] A tetrazolinone compound in which R3 is a C1- C3 haloalkoxy group and Q is Q12 in [Aspect 2],

[00590] A tetrazolinone compound in which R3 is a methyl group and Q is Q12 in [Aspect 2].

[00591] A tetrazolinone compound in which R3 is an ethyl group and Q is Q12 in [Aspect 2],

[00592] A tetrazolinone compound in which R3 is a cyclopropyl group and Q is Q12 in [Aspect 2].

[00593] A tetrazolinone compound in which R3 is a chlorine atom and Q is Q12 in [Aspect 2].

[00594] A tetrazolinone compound in which R3 is a bromine atom and Q is Q12 in [Aspect 2],

[00595] A tetrazolinone compound in which R3 is a methoxy group and Q is Q12 in [Aspect 2].

[Aspect 3]

[00596] A tetrazolinone compound in which A is of formula (2), R37 is a halogen atom; R38, R39, R40, and R41 each independently represent a hydrogen atom or a halogen atom; R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1- C3 alkoxy group, a C2-C3 alkynyl group, or a C1-C3 haloalkoxy group; R7 is a methyl group; and X is an oxygen atom.

[Aspect 4]

[00597] A tetrazolinone compound in which A is of formula (2), R37 is a C1-C3 alkoxy group; R38, R39, R40, and R41 each independently represent a hydrogen atom or a halogen atom; R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1- C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C2-C3 alkynyl group, or a C1-C3 haloalkoxy group; R7 is a methyl group; and X is an oxygen atom.

[Aspect 5]

[00598] A tetrazolinone compound in which A is of formula (2), R37 is a C1-C3 haloalkoxy group; R38, R39, R40, and R41 each independently represent a hydrogen atom or a halogen atom; R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C2-C3 alkynyl group, or a C1-C3 haloalkoxy group; R7 is a methyl group; and X is an oxygen atom.

[00599] A tetrazolinone compound in which A is of formula (2), R37 is a C1-C3 alkoxy group or a C1-C3 haloalkoxy group; R38, R39, R40, and R41 each independently represent a hydrogen atom or a halogen atom; R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C1-C3 alkoxy group, a C2-C3 alkynyl group, or a C1-C3 haloalkoxy group; R7 is a methyl group; and X is an oxygen atom.

[00600] A tetrazolinone compound in which Q is Q1 in [Aspect 3] -

[00601] A tetrazolinone compound in which Q is Q1 in [Aspect 4] -

[00602] A tetrazolinone compound in which Q is Q1 in [Aspect 5] -

[00603] A tetrazolinone compound in which Q is Q2 in [Aspect 3] -

[00604] A tetrazolinone compound in which Q is Q2 in [Aspect 4] -

[00605] A tetrazolinone compound in which Q is Q2 in [Aspect 5] -

[00606] A tetrazolinone compound in which Q is Q3 in [Aspect 3] -

[00607] A tetrazolinone compound in which Q is Q3 in [Aspect 4] -

[00608] A tetrazolinone compound in which Q is Q3 in [Aspect 5].

[00609] A tetrazolinone compound in which Q is Q4 in [Aspect 3].

[00610] A tetrazolinone compound in which Q is Q4 in [Aspect 4].

[00611] A tetrazolinone compound in which Q is Q4 in [Aspect 5].

[00612] A tetrazolinone compound in which Q is Q5 in [Aspect 3].

[00613] A tetrazolinone compound in which Q is Q5 in [Aspect 4].

[00614] A tetrazolinone compound in which Q is Q5 in [Aspect 5].

[00615] A tetrazolinone compound in which Q is Q6 in [Aspect 3].

[00616] A tetrazolinone compound in which Q is Q6 in [Aspect 4].

[00617] A tetrazolinone compound in which Q is Q6 in [Aspect 5].

[00618] A tetrazolinone compound in which Q is Q7 in [Aspect 3].

[00619] A tetrazolinone compound in which Q is Q7 in [Aspect 4].

[00620] A tetrazolinone compound in which Q is Q7 in [Aspect 5].

[00621] A tetrazolinone compound in which Q is Q8 in [Aspect 3].

[00622] A tetrazolinone compound in which Q is Q8 in [Aspect 4].

[00623] A tetrazolinone compound in which Q is Q8 in [Aspect 5].

[00624] A tetrazolinone compound in which Q is Q9 in [Aspect 3].

[00625] A tetrazolinone compound in which Q is Q9 in [Aspect 4].

[00626] A tetrazolinone compound in which Q is Q9 in [Aspect 5] -

[00627] A tetrazolinone compound in which Q is Q10 in [Aspect 3],

[00628] A tetrazolinone compound in which Q is Q10 in [Aspect 4],

[00629] A tetrazolinone compound in which Q is Q10 in [Aspect 5],

[00630] A tetrazolinone compound in which Q is Q11 in [Aspect 3],

[00631] A tetrazolinone compound in which Q is Q11 in [Aspect 4],

[00632] A tetrazolinone compound in which Q is Q11 in [Aspect 5],

[00633] A tetrazolinone compound in which Q is Q12 in [Aspect 3],

[00634] A tetrazolinone compound in which Q is Q12 in [Aspect 4],

[00635] A tetrazolinone compound in which Q is Q12 in [Aspect 5],

[00636] A tetrazolinone compound of formula (1) in which R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, a C2-C9 heterocyclyl group optionally having one or more atoms or groups selected from Group P, or a C3-C12 cycloalkenyl group optionally having one or more atoms or groups selected from Group P.

[00637] A tetrazolinone compound of formula (1) in which R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C6-C16 aryl group, a C2-C9 heterocyclyl group, or a C3-C12 cycloalkenyl group (as long as the C6-C16 aryl group, the C2-C9 heterocyclyl group, and the C3-C12 cycloalkenyl group optionally have one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1- C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group , a nitro group, an amino group optionally having a C1-C6 alkyl group, a cyano group, and a C6-C16 aryloxy group).

[00638] A tetrazolinone compound of formula (1) in which Q is Q1; R1, R2, R4, R5, R6, R8, R9, and R10 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; A is a C6-C16 aryl group, a C2-C9 heterocyclyl group, or a C3-C12 cycloalkenyl group (as long as the C6-C16 aryl group, the C2-C9 heterocyclyl group, and the C3-C12 cycloalkenyl group optionally have a or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a nitro group, an amino group optionally having a C1-C6 alkyl group, a cyano group, and a C6-C16 aryloxy group).

[00639] A tetrazolinone compound of formula (1) in which Q is Q1; R1, R2, R4, R5, R6, R8, R9, and R10 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C2-C9 heterocyclyl group or a C3-C12 cycloalkenyl group (provided that the C2-C9 heterocyclyl group and the C3-C12 cycloalkenyl group optionally have one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, and a C1-C6 alkoxy group.

[00640] A tetrazolinone compound of formula (1) in which Q is Q1; R1, R2, R4, R5, R6, R8, R9, and R10 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C6-C16 aryl group (provided that the C6-C16 aryl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a nitro group, an amino group optionally having a C1-C6 alkyl group, a cyano group, and a C6-C16 aryloxy group).

[00641] A tetrazolinone compound of formula (1) in which Q is Q2; R1, R2, R4, R5, R6, R12, and R13 are hydrogen atoms; R11 is a hydrogen atom or a halogen atom; R14 is a hydrogen atom or a C1-C6 alkyl group; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C6-C16 aryl group, a C2-C9 heterocyclyl group, or a C3-C12 cycloalkenyl group (as long as the C6-C16 aryl group, the C2-C9 heterocyclyl group, and the optionally C3-C12 cycloalkenyl group - have one or more atoms or groups selected from the group consisting of an amino group optionally having a C1-C6 alkyl group, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group , a C1-C6 haloalkoxy group, and a C1-C6 alkylthio group).

[00642] A tetrazolinone compound of formula (1) in which Q is Q2; R1, R2, R4, R5, R6, R12, and R13 are hydrogen atoms; R11 is a hydrogen atom or a halogen atom; R14 is a hydrogen atom or a C1-C6 alkyl group; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C2-C9 heterocyclyl group or a C3-C12 cycloalkenyl group (provided that the C2-C9 heterocyclyl group and the C3-C12 cycloalkenyl group optionally have one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, and a C1-C6 alkoxy group.

[00643] A tetrazolinone compound of formula (1) in which Q is Q2; R1, R2, R4, R5, R6, R12, and R13 are hydrogen atoms; R11 is a hydrogen atom or a halogen atom; R14 is a hydrogen atom or a C1-C6 alkyl group; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C6-C16 aryl group (provided that the C6-C16 aryl group optionally has one or more atoms or groups selected from the group consisting of an amino group optionally having a C1-C6 alkyl group, a halogen atom, a group C1-C6 alkyl, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, and a C1-C6 alkylthio group).

[00644] A tetrazolinone compound of formula (1) in which R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C6-C16 aryl group or a C2-C9 heterocyclyl group (provided that the C6-C16 aryl group and the C2-C9 heterocyclyl group optionally have one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, and a C1-C6 alkoxy group).

[00645] A tetrazolinone compound of formula (1) in which R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C6-C16 aryl group (provided that the C6-C16 aryl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, and a C1-C6 alkoxy group) .

[00646] A tetrazolinone compound of formula (1) in which R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a methyl group; X is an oxygen atom; and A is a C2-C9 heterocyclyl group (provided that the C2-C9 heterocyclyl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, and a C1-C6 alkoxy group ).

[Aspect 6]

[00647] A tetrazolinone compound of formula (1) in which Q is Q1; R1, R2, R4, R5, R6, R8, R9, and R10 are hydrogen atoms; R3 is a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group, a pyridinyl group, a benzoxazolyl group, a quinolyl group, a piperidinyl group, a morpholinyl group, a piperazinyl group, or a cyclohexenyl group (as long as the phenyl group, the pyridinyl group, the group benzoxazolyl, quinolinyl group, piperidinyl group, morpholinyl group, piperazinyl group, and cyclohexenyl group optionally have one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, one C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, a nitro group, an amino group optionally having a C1-C6 alkyl group, a cyano group, a formyl group , a C2-C6 alkylcarbonyl group, a C2-C6 alkoxycarbonyl group, a C1- C6 alkylsulfonyl group, an aminosulfonyl group optionally having a C1-C6 alkyl group, and a phenoxy group).

[00648] A tetrazolinone compound in which R3 is a C1- C6 alkyl group and A is a phenyl group in [Aspect 6],

[00649] A tetrazolinone compound in which R3 is a C3-C6 cycloalkyl group and A is a phenyl group in [Aspect 6].

[00650] A tetrazolinone compound in which R3 is a halogen atom and A is a phenyl group in [Aspect 6],

[00651] A tetrazolinone compound in which R3 is a C1- C6 alkoxy group and A is a phenyl group in [Aspect 6],

[00652] A tetrazolinone compound in which R3 is a C1- C6 alkyl group and A is a quinolyl group in [Aspect 6].

[Aspect 7]

[00653] A tetrazolinone compound of formula (1) in which Q is Q2; R11, R12, R13, and R14 each independently represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group; R1, R2, R4, R5, and R6 are hydrogen atoms; R3 is a 1- C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group, a pyridinyl group, a benzo [1,3] dioxol-5-yl group, a benzoxazolyl group, a quinolyl group, a pyrimidinyl group, a pyridazinyl group, or a cyclohexenyl group ( provided that the phenyl group, the pyridinyl group, the benzo [1,3] dioxol-5-yl group, the benzoxazolyl group, the quinolyl group, the pyrimidinyl group, the pyridazinyl group, and the cyclohexenyl group optionally have a or more atoms or groups selected from the group consisting of a halogen atom, a C1-C6 alkyl group, a C1- C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C1-C6 alkylthio group, and an amino group optionally having a C1-C6 alkyl group).

[00654] A tetrazolinone compound in which R3 is a C1- C6 alkyl group and A is a phenyl group in [Aspect 7],

[00655] A tetrazolinone compound in which R3 is a C3-C6 cycloalkyl group and A is a phenyl group in [Aspect 7],

[00656] A tetrazolinone compound in which R3 is a halogen atom and A is a phenyl group in [Aspect 7],

[00657] A tetrazolinone compound in which R3 is a C1- C6 alkoxy group and A is a phenyl group in [Aspect 7],

[00658] A tetrazolinone compound of formula (1) in which Q is Q3; R1, R2, R4, R5, R6, R15, and R16 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group optionally having a C1-C6 alkoxy group.

[00659] A tetrazolinone compound of formula (1) in which Q is Q4; R1, R2, R4, R5, R6, R17, and R18 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group (provided that the phenyl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom and a C1-C6 alkoxy group).

[00660] A tetrazolinone compound of formula (1) in which Q is Q5; R1, R2, R4, R5, R6, R19, and R20 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group (provided that the phenyl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom and a C1-C6 alkoxy group).

[00661] A tetrazolinone compound of formula (1) in which Q is Q6; R1, R2, R4, R5, R6, and R21 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group optionally having a C1-C6 alkoxy group.

[00662] A tetrazolinone compound of formula (1) in which Q is Q7; R1, R2, R4, R5, R6, R22, and R23 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group (provided that the phenyl group optionally has one or more atoms or groups selected from the group consisting of a cyano group, a C1-C6 alkoxy group, and an amino group optionally having a C1-C6 alkyl group).

[00663] A tetrazolinone compound of formula (1) in which Q is Q8; R1, R2, R4, R5, R6, R24, and R25 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group (provided that the phenyl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom and a C1-C6 alkoxy group).

[00664] A tetrazolinone compound of formula (1) in which Q is Q9; R1, R2, R4, R5, R6, R27, R28, and R29 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group (provided that the phenyl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom and a C1-C6 alkoxy group).

[00665] A tetrazolinone compound of formula (1) in which Q is Q10; R1, R2, R4, R5, R6, R30, R31, and R32 are hydrogen atoms; R3 is a C1-C6 alkyl group; R7 is a C1-C6 alkyl group; X is an oxygen atom; and A is a phenyl group (provided that the phenyl group optionally has one or more atoms or groups selected from the group consisting of a halogen atom and a C1-C6 alkoxy group).

[Aspect 81

[00666] A tetrazolinone compound of formula (1) in which A is of formula (2), Q is Q1,

[00667] R37 is a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group, R38, R39, and R40 are hydrogen atoms ; R41 is a C1-C3 alkoxy group or a C1-C3 haloalkoxy group; R1, R2, R4, R5, and R6 are hydrogen atoms; R7 is a methyl group; R8, R9, and R10 are hydrogen atoms or halogen atoms; and X is an oxygen atom.

[00668] A tetrazolinone compound in which R3 is a C1- C6 alkyl group in [Aspect 8],

[00669] A tetrazolinone compound in which R3 is a C3-C6 cycloalkyl group in [Aspect 8],

[00670] A tetrazolinone compound in which R3 is a halogen atom in [Aspect 8],

[00671] A tetrazolinone compound in which R3 is a C1- C6 alkoxy group in [Aspect 8],

[00672] A tetrazolinone compound of formula (1) in which A is of formula (4).

[Aspect 9]

[00673] A tetrazolinone compound in which A is of formula (4),

[00674] R42 is a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, or a C1-C6 haloalkoxy group; R43 and R44 are hydrogen atoms; R45 is a C1-C3 alkoxy group or a C1-C3 haloalkoxy group; R1, R2, R4, R5, and R6 are hydrogen atoms; R7 is a methyl group; and X is an oxygen atom.

[00675] A tetrazolinone compound in which R3 is a C1- C6 alkyl group and Q is Q1 in [Aspect 9],

[00676] A tetrazolinone compound in which R3 is a C3-C6 cycloalkyl group and Q is Q1 in [Aspect 9],

[00677] A tetrazolinone compound in which R3 is a halogen atom and Q is Q1 in [Aspect 9],

[00678] A tetrazolinone compound in which R3 is a C1- C6 alkoxy group and Q is Q1 in [Aspect 9],

[00679] A tetrazolinone compound in which R3 is a C1- C6 alkyl group and Q is Q2 in [Aspect 9],

[00680] A tetrazolinone compound in which R3 is a C3-C6 cycloalkyl group and Q is Q2 in [Aspect 9],

[00681] A tetrazolinone compound in which R3 is a halogen atom and Q is Q2 in [Aspect 9],

[00682] A tetrazolinone compound in which R3 is a C1- C6 alkoxy group and Q is Q2 in [Aspect 9],

[00683] As used herein, the compounds represented by the general formulas include individual stereoisomers and mixtures of stereoisomers, such as all active geometric isomers and optical isomers.

[00684] Next, a process for producing the present compound will be described.

[00685] The present compound can be produced, for example, by the following Production Processes.

(Production Process A)

[00686] The present compound represented by formula (1) (hereinafter referred to as compound (1)) can be produced by reacting a compound represented by formula (A1) (hereinafter referred to as compound (A1)) with a compound represented by formula (A2) (hereinafter referred to as compound (A2)) in the presence of a base:

[00687] where R1, R2, R3, R4, R5, R6, R7, X, A, and Q are the same as defined above, and Z11 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, or a p-toluenesulfonyloxy group.

[00688] The reaction is usually carried out in a solvent.

[00689] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; Water; and mixtures thereof.

[00690] Examples of the base to be used in the reaction include organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates, such as sodium hydrogen carbonate; alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal halides, such as sodium fluoride, potassium fluoride, and cesium fluoride; alkali metal hydrides, such as lithium hydride, sodium hydride, and potassium hydride; and alkali metal alkoxides, such as sodium tert-butoxide and potassium tert-butoxide.

[00691] In the reaction, the compound (A2) is generally used in production within a range of 1 to 10 moles, and the base is generally used in proportion within a range of 0.5 to 5 moles, based on 1 mol of compound (A1).

[00692] The reaction temperature of the reaction is usually within a range of -20 to 150 ° C. The reaction time is usually within the range of 0.1 to 24 hours.

[00693] If necessary, sodium iodide, tetrabutylammonium iodide, and the like can be added in the reaction, and these compounds are generally used in the proportion of 0.001 to 1.2 moles, based on 1 mol of the compound (A1).

[00694] After the completion of the reaction, the compound (1) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The present isolated compound can also be purified by chromatography, recrystallization, and the like.

(Production Process B)

[00695] Among the compounds (1), a compound in which A is A1 (hereinafter referred to as compound (1-1)) can be produced by submitting a compound represented by formula (B1) (hereinafter referred to as compound (B1) ) and a compound represented by formula (B2) (hereinafter referred to as the compound (B2)) to a coupling reaction in the presence of a base and a catalyst:

[00696] where R1, R2, R3, R4, R5, R6, R7, X, and Q are the same as defined above, A1 represents a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, a C2-C9 heteroaryl group optionally having one or more atoms or groups selected from Group P, a C3-C12 cycloalkyl group optionally having one or more atoms or groups selected from Group P, or a C3-C12 cycloalkenyl group optionally having one or more atoms or groups selected from Group P, Z21 represents a chlorine atom, a bromine atom, or an iodine atom, and Z31 represents B (OH) 2, an alkoxyboryl group, or BF3 K + trifluoroborate.

[00697] The reaction is usually carried out in a solvent.

[00698] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; alcohols, such as methanol, ethanol, propanol, and butanol; Water; and mixtures thereof.

[00699] It is usually possible to use, as the compound (B2) to be used in the reaction, commercially available compounds, or compounds produced by a known method mentioned in N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457. It is possible to produce the compound (B2) which is a boronic acid ester derivative, for example, by reacting an iodine compound (A1-1) or a bromine compound (A1- Br) with an alkillithium, such as butyllithium, followed by a reaction with a boric acid ester. It is possible to produce the compound (B2), which is a boronic acid ester derivative, optionally hydrolyzing the compound (B2) as the boric acid ester derivative obtained in the reaction mentioned above. It is also possible to produce the compound (B2), which is trifluoroborate BF3 K +, by fluorination of a certain compound (B2) with potassium hydrogen fluoride according to a known method mentioned in Molander and another Acc. Chem. Res., 2007, 40, 275.

[00700] Examples of the catalyst to be used in the reaction between the compound (B1) and the compound (B2) include palladium (II) acetate, dichlorobis (triphenylphosphine) palladium, tetracistriphenylphosphinapalladium (O), palladium acetate (liytrisciclo- hexylphosphine, bis (diphenylphosphineferrocenyl) palladium (ll) dichloride, tris (dibenzylidene acetone) dipaladium, and the like.

[00701] Examples of the base to be used in the reaction between compound (B1) and compound (B2) include organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates, such as sodium hydrogen carbonate; alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal halides, such as sodium fluoride, potassium fluoride, and cesium fluoride; alkali metal hydrides, such as lithium hydride, sodium hydride, and potassium hydride; alkali metal phosphates, such as tripotassium phosphate; and alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.

[00702] In the reaction between the compound (B1) and the compound (B2), the compound (B2) is usually used in proportion within a range of 1 to 10 moles, the base is usually used in proportion within a range of 1 to 10 moles, and the catalyst is usually used in the proportion within a range of 0.0001 to 1 mole, based on 1 mole of the compound (B1).

[00703] The reaction temperature of the reaction between the compound (B1) and the compound (B2) is usually within a range of 0 to 150 ° C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00704] After completion of the reaction, the present compound represented by formula (1-1) can be isolated by performing post-treatment operations, such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound present can also be purified by chromatography, re-crystallization, and the like.

(Production Process C)

[00705] Among the compounds (1), a compound in which A is A2 (hereinafter referred to as the compound (1-2)) can be produced by submitting a compound represented by formula (B1) and a compound represented by formula (C1) (hereinafter referred to as the compound (C1)) to a coupling reaction in the presence of a base and a catalyst:

[00706] wherein R1, R2, R3, R4, R5, R6, R7, X, Q, and Z21 are the same as defined above, and A2 represents a heterocyclyl C2-C9 group optionally having one or more atoms or groups selected from the Group P (as long as the heterocyclyl group optionally has, as a ring constituent atom, one or more nitrogen atoms and also one or more oxygen atoms or sulfur atoms, and nitrogen and hydrogen atoms making up the heterocyclyl group are linked together to others).

[00707] The reaction is usually carried out in a solvent.

[00708] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof.

[00709] It is usually possible to use, as the compound (C1) to be used in the reaction, commercially available compounds. Specific examples thereof include morpholine, piperidine, piperazine, N-methylpiperazine, thiomorpholine, n-propyl bromide, pyrrolidine, ethylenedimine, azacyclobutane, hexamethyleneimine, pyrrole, imidazole, pyrazole, and the like. Examples of the catalyst to be used in the reaction include copper (I) iodide, copper (II) acetate, cobalt (II) chloride, palladium (II) acetate, dichlorobis (triphenylphosphine) palladium, tetracistriphenylphosphinapalladium (O), palladium (ll) acetate Ztrisciclohexylphosphine, bis (diphenylphosphineferrocenyl) dichloride palladium (ll), and tris (dibenzylidenoacetone) dipaladium.

[00710] Examples of the base to be used in the reaction include organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates, such as sodium hydrogen carbonate; alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal halides, such as sodium fluoride, potassium fluoride, and cesium fluoride; alkali metal hydrides, such as lithium hydride, sodium hydride, and potassium hydride; alkali metal hydrides, such as lithium hydride, sodium hydride, and potassium hydride; and alkali metal alkoxides, such as sodium tert-butoxide and potassium tert-butoxide.

[00711] In the reaction, the compound (C1) is usually used in the proportion within a range of 1 to 10 moles, the catalyst is usually used in the proportion within a range of 0.001 to 5 mol, and the base is usually used in proportion within a range of 1 to 10 moles, based on 1 mole of the compound (B1).

[00712] If necessary, binders, such as 1,10-phenanthroline and tetraethylethylenediamine can be added in the reaction, and these compounds are usually used in the proportion of 0.001 to 5 moles based on the 1 mole of the compound (B1).

[00713] The reaction temperature of the reaction is usually within a range of -20 to 150 ‘C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00714] After completion of the reaction, the present compound represented by formula (1-2) can be isolated by performing post-treatment operations, such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound present can also be purified by chromatography, re-crystallization, and the like.

(Production Process D)

[00715] Among the compounds (1), a compound in which R7 is a hydrogen atom (hereinafter referred to as the compound (1-3)) can be produced by reacting a compound represented by the formula (D1) (hereinafter referred to as the compound (D1)) with a azidating agent:

[00716] where the symbols are the same as defined above.

[00717] The reaction is usually carried out in a solvent.

[00718] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof.

[00719] Examples of the azidation agent to be used in the reaction include inorganic azides, such as sodium azide, barium azide, and lithium azide; and organic azides, such as trimethylsilyl azide and diphenylphosphoryl azide.

[00720] In the reaction, the azidation agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (D1).

[00721] The reaction temperature of the reaction is usually within a range of -20 to 150 'C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00722] If necessary, Lewis acid, such as aluminum chloride or zinc chloride can be added in the reaction, and these compounds are usually used in the proportion of 0.05 to 5 moles based on the 1 mol of the compound (D1) .

[00723] After completion of the reaction, the present compound represented by formula (1-3) can be isolated by performing post-treatment operations, such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound present can also be purified by chromatography, re-crystallization, and the like.

[00724] (Production Process E)

[00725] The compound (1) can be produced by reacting the compound (1-3) with a compound represented by the formula (E1) (hereinafter referred to as the compound (E1)) in the presence of a base:

[00726] in which the symbols are the same as defined above.

[00727] The reaction is usually carried out in a solvent.

[00728] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; Water; and mixtures thereof.

[00729] It is usually possible to use, as the compound (E1) to be used in the reaction, commercially available products. Specific examples thereof include alkyl halides, such as chlorodifluoromethane, methyl bromide, ethyl bromide, n-propyl bromide, methyl iodide, ethyl iodide, n-propyl bromide, allyl bromide, cyclopropyl bromide , and 1,1-difluoro-2-iodoethane; dialkyl sulfates, such as dimethyl sulfate; and arylsulfonic acid or alkyl esters, such as methyl p-toluenesulfonate, ethyl p-toluenesulfonate, n-propyl p-toluenesulfonate, methyl methanesulfonate, ethyl methanesulfonate, and n-propyl methanesulfonate.

[00730] Examples of the base to be used in the reaction include organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates, such as sodium hydrogen carbonate; alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal halides, such as sodium fluoride, potassium fluoride, and cesium fluoride; alkali metal hydrides, such as lithium hydride, sodium hydride, and potassium hydride; alkali metal hydrides, such as lithium hydride, sodium hydride, and potassium hydride; and alkali metal alkoxides, such as sodium tert-butoxide and potassium tert-butoxide.

[00731] In the reaction, the compound (E1) is usually used in the proportion within a range of 1 to 10 moles and the base is usually used in the proportion within a range of 1 to 10 moles, based on the 1 mol of the compound (1-3).

[00732] The reaction temperature of the reaction is usually within a range of -20 to 150 ‘C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00733] After completion of the reaction, the compound (1) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound present can also be purified by chromatography, recrystallization, and the like.

(Production Process F)

[00734] Among the compounds (1), a compound in which X is a sulfur atom (hereinafter referred to as the compound (1-S)) can be produced by a known sulfidation reaction of a compound in which X is an atom oxygen (hereinafter referred to as the compound (1-O)) of the present compounds represented by formula (1):

[00735] in which the symbols are the same as defined above.

[00736] The reaction is usually carried out in a solvent.

[00737] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; nitriles, such as acetonitrile; and mixtures thereof.

[00738] Examples of the sulfurizing agent to be used in the reaction include phosphorus pentasulfide and Lawesson's reagent (2,4-Bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphetane 2,4-disulfide).

[00739] In the reaction, the sulfurizing agent is preferably used in the proportion within a range of 0.5 to 1.5 moles based on the 1 mole of the compound (1-0).

[00740] The reaction temperature of the reaction is usually within a range of -20 to IδO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00741] If necessary, organic bases, such as pyridine and trimethylamine; and inorganic bases, such as alkali metal hydroxide and alkali metal carbonate can be added in the reaction, and the amount of the base to be added is within a range of 0.5 to 1.5 moles based on the compound ( 1-O).

[00742] After completion of the reaction, the present compound represented by formula (1-S) can be isolated by performing post-treatment operations, such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound present can also be purified by chromatography, re-crystallization, and the like.

(Production Process G)

[00743] Among the compounds (1), a compound represented by formula (1-4) in which R3 is R71 (hereinafter referred to as compound (1-4)) can be produced by submitting a compound represented by formula (G1) ( hereinafter referred to as the compound (G1)) and a compound represented by formula (G21) (hereinafter referred to as the compound (G21)) to a coupling reaction in the presence of a base and a catalyst:

[00744] where R1, R2, R4, R5, R6, R7, X, A, Q, and Z31 are the same as defined above, Z41 represents a chlorine atom, a bromine atom, an iodine atom, or a group trifluoromethanesulfonyloxy, and R71 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3 group -C6 cycloalkyl, or a C3-C6 halocycloalkyl group.

[00745] The reaction can be performed according to the reaction mentioned in Production Process B.

[00746] Among the compounds (1), a compound represented by formula (1-5) in which R4 is R72 (hereinafter referred to as the compound (1-5)) can be produced by submitting a compound represented by formula (G2) ( hereinafter referred to as the compound (G2)) and a compound represented by formula (G22) (hereinafter referred to as the compound (G22)) to a coupling reaction in the presence of a base and a catalyst:

[00747] where R1, R2, R3, R5, R6, R7, X, A, Q, Z31 and Z41 are the same as defined above, and R72 represents a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C3-C5 cycloalkyl group, or a C3-C5 halocycloalkyl group.

[00748] The reaction can be performed according to the reaction mentioned in Production Process B.

[00749] Among the compounds (1), a compound represented by formula (1-6) in which R5 is R72 (hereinafter referred to as the compound (1-6)) can be produced according to the reaction mentioned in the Production Process B, using a compound represented by formula (G3) (hereinafter referred to as compound (G3)) and compound (G22):

[00750] in which the symbols are the same as defined above.

[00751] Among the compounds (1), a compound represented by formula (1-7) in which R6 is R72 (hereinafter referred to as the compound (1-7)) can be produced according to the reaction mentioned in the Production Process B, using a compound represented by formula (G4) (hereinafter referred to as compound (G4)) and compound (G22):

[00752] where the symbols are the same as defined above.

[00753] Among the compounds (1), a compound in which two or more substituents selected from R3, R4, R5, and R6 are R71 and / or R72 can be produced according to Production Process B.

[00754] It is also possible to produce the compound (1-4), the compound (1-5), the compound (1-6), and the compound (1-7) using the other known coupling reaction in place of the reaction Production Process coupling B.

(Production Process H)

[00755] Among the compounds (1), a compound represented by formula (1-8) in which Q is Q1 and R8 is R73 (hereinafter referred to as the compound (1-8)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (H1) (hereinafter referred to as compound (H1)) and a compound represented by formula (H21) (hereinafter referred to as compound (H21)):

[00756] wherein R1, R2, R3, R4, R5, R6, R7, R9, R10, X, A, Z31, and Z41 are the same as defined above, and R73 represents a C1-C6 alkyl group optionally having a group selected from Group P1, a C3-C6 cycloalkyl group having a group selected from Group P1, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, or a C2-C6 haloalkynyl group.

em que os símbolos são iguais ao definido acima.[00757] Among the compounds (1), a compound represented by formula (1-9) in which Q is Q1 and R9 is R73 (hereinafter referred to as the compound (1-9)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (H2) (hereinafter referred to as compound (H2)) and compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00758] Among the compounds (1), a compound represented by formula (1-10) in which Q is Q1 and R10 is R73 (hereinafter referred to as the compound (1-10)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (H3) (hereinafter referred to as the compound (H3)) and the compound (H21):

where the symbols are the same as defined above.

[00759] Among the compounds (1), a compound in which two or more substituents selected from R8, R9, and R10 are R73 can be produced according to Production Process B.

[00760] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process I)

em que os símbolos são iguais ao definido acima.[00761] Among the compounds (1), a compound represented by formula (1-11) in which Q is Q2 and R11 is R73 (hereinafter referred to as the compound (1-11)) can be produced according to the reaction mentioned - nothing in Production Process B, using a compound represented by formula (11) (hereinafter referred to as compound (11)) and compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00762] Among the compounds (1), a compound represented by formula (1-12) in which Q is Q2 and R12 is R73 (hereinafter referred to as the compound (1-12)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (I2) (hereinafter referred to as compound (I2)) and compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00763] Among the compounds (1), a compound represented by formula (1-13) in which Q is Q2 and R13 is R73 (hereinafter referred to as the compound (1-13)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (I3) (hereinafter referred to as compound (I3)) and compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00764] Among the compounds (1), a compound represented by formula (1-14) in which Q is Q2 and R14 is R73 (hereinafter referred to as the compound (1-14)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (I4) (hereinafter referred to as compound (I4)) and compound (H21):

where the symbols are the same as defined above.

[00765] Among the compounds (1), a compound in which two or more substituents selected from R11, R12, R13, and R14 are R73 can be produced according to Production Process B.

[00766] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process J)

em que os símbolos são iguais ao definido acima.[00767] Among the compounds (1), a compound represented by formula (1-15) in which Q is Q3 and R15 is R73 (hereinafter referred to as the compound (1-15)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (J1) (hereinafter referred to as the compound (J1)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00768] Among the compounds (1), a compound represented by formula (1-16) in which Q is Q3 and R16 is R73 (hereinafter referred to as the compound (1-16)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (J2) (hereinafter referred to as the compound (J2)) and the compound (H21):

where the symbols are the same as defined above.

[00769] Among the compounds (1), a compound in which R15 and R16 are R73 can be produced according to Production Process B.

[00770] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process K)

em que os símbolos são iguais ao definido acima.[00771] Among the compounds (1), a compound represented by formula (1-17) in which Q is Q4 and R17 is R73 (hereinafter referred to as the compound (1-17)) can be produced according to the reaction mentioned - nothing in Production Process B, using a compound represented by formula (K1) (hereinafter referred to as compound (K1)) and compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00772] Among the compounds (1), a compound represented by formula (1-18) in which Q is Q4 and R18 is R73 (hereinafter referred to as the compound (1-18)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (K2) (hereinafter referred to as the compound (K2)) and the compound (H21):

where the symbols are the same as defined above.

[00773] Among the compounds (1), a compound in which R1 / and R18 are R73 can be produced according to Production Process B.

[00774] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process L)

em que os símbolos são iguais ao definido acima.[00775] Among the compounds (1), a compound represented by formula (1-19) in which Q is Q5 and R19 is R73 (hereinafter referred to as the compound (1-19)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (L1) (hereinafter referred to as the compound (L1)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00776] Among the compounds (1), a compound represented by formula (1-20) in which Q is Q5 and R20 is R73 (hereinafter referred to as the compound (1-20)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (L2) (hereinafter referred to as the compound (L2)) and the compound (H21):

where the symbols are the same as defined above.

[00777] Among the compounds (1), a compound in which R19 and R20 are R73 can be produced according to Production Process B.

[00778] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process M)

em que os símbolos são iguais ao definido acima.[00779] Among the compounds (1), a compound represented by formula (1-21) in which Q is Q6 and R21 is R73 (hereinafter referred to as the compound (1-21)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (M1) (hereinafter referred to as the compound (M1)) and the compound (H21):

where the symbols are the same as defined above.

[00780] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process N)

em que os símbolos são iguais ao definido acima.[00781] Among the compounds (1), a compound represented by formula (1-22) in which Q is Q7 and R22 is R73 (hereinafter referred to as the compound (1-22)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (N1) (hereinafter referred to as the compound (N1)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00782] Among the compounds (1), a compound represented by formula (1-23) in which Q is Q7 and R23 is R73 (hereinafter referred to as the compound (1-23)) can be produced according to the reaction mentioned - nothing in Production Process B, using a compound represented by formula (N2) (hereinafter referred to as the compound (N2)) and the compound (H21):

where the symbols are the same as defined above.

[00783] Among the compounds (1), a compound in which R22 and R23 are R73 can be produced according to Production Process B.

[00784] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(O Production Process)

em que os símbolos são iguais ao definido acima.[00785] Among the compounds (1), a compound represented by formula (1-24) in which Q is Q8 and R24 is R73 (hereinafter referred to as the compound (1-24)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (01) (hereinafter referred to as compound (01)) and compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00786] Among the compounds (1), a compound represented by formula (1-25) in which Q is Q8 and R25 is R / 3 (hereinafter referred to as the compound (1-25)) can be produced according to reaction mentioned in Production Process B, using a compound represented by formula (02) (hereinafter referred to as compound (02)) and compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00787] Among the compounds (1), a compound represented by formula (1-26) in which Q is Q8 and R26 is R73 (hereinafter referred to as the compound (1-26)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (03) (hereinafter referred to as compound (03)) and compound (H21):

where the symbols are the same as defined above.

[00788] Among the compounds (1), a compound in which two or more substituents selected from R24, R25, and R26 are R73 can be produced according to Production Process B.

[00789] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process P)

em que os símbolos são iguais ao definido acima.[00790] Among the compounds (1), a compound represented by formula (1-27) in which Q is Q9 and R27 is R73 (hereinafter referred to as the compound (1-27)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (P1) (hereinafter referred to as the compound (P1)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00791] Among the compounds (1), a compound represented by formula (1-28) in which Q is Q9 and R28 is R73 (hereinafter referred to as the compound (1-28)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (P2) (hereinafter referred to as the compound (P2)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00792] Among the compounds (1), a compound represented by formula (1-29) in which Q is Q9 and R29 is R73 (hereinafter referred to as the compound (1-29)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (P3) (hereinafter referred to as the compound (P3)) and the compound (H21):

where the symbols are the same as defined above.

[00793] Among the compounds (1), a compound in which two or more substituents selected from R27, R28, and R29 are R73 can be produced according to Production Process B.

[00794] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Q Production Process)

em que os símbolos são iguais ao definido acima.[00795] Among the compounds (1), a compound represented by formula (1-30) in which Q is Q10 and R30 is R73 (hereinafter referred to as the compound (1-30)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (R1) (hereinafter referred to as the compound (R1)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00796] Among the compounds (1), a compound represented by formula (1-31) in which Q is Q10 and R31 is R73 (hereinafter referred to as the compound (1-31)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (R2) (hereinafter referred to as the compound (R2)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00797] Among the compounds (1), a compound represented by formula (1-32) in which Q is Q10 and R32 is R73 (hereinafter referred to as the compound (1-32)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (R3) (hereinafter referred to as the compound (R3)) and the compound (H21):

where the symbols are the same as defined above.

[00798] Among the compounds (1), a compound in which two or more substituents selected from R30, R31, and R32 are R73 can be produced according to Production Process B.

[00799] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process R)

em que os símbolos são iguais ao definido acima.[00800] Among the compounds (1), a compound represented by formula (1-33) in which Q is Q11 and R33 is R73 (hereinafter referred to as the compound (1-33)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (S1) (hereinafter referred to as the compound (S1)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00801] Among the compounds (1), a compound represented by formula (1-34) in which Q is Q11 and R34 is R73 (hereinafter referred to as the compound (1-34)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (S2) (hereinafter referred to as the compound (S2)) and the compound (H21):

where the symbols are the same as defined above.

[00802] Among the compounds (1), a compound in which R33 and R34 are R73 can be produced according to Production Process B.

[00803] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

(Production Process S)

em que os símbolos são iguais ao definido acima.[00804] Among the compounds (1), a compound represented by formula (1-35) in which Q is Q12 and R35 is R73 (hereinafter referred to as the compound (1-35)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (T1) (hereinafter referred to as the compound (T1)) and the compound (H21):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00805] Among the compounds (1), a compound represented by formula (1-36) in which Q is Q12 and R36 is R73 (hereinafter referred to as the compound (1-36)) can be produced according to the mentioned reaction in Production Process B, using a compound represented by formula (T2) (hereinafter referred to as the compound (T2)) and the compound (H21):

where the symbols are the same as defined above.

[00806] Among the compounds (1), a compound in which R35 and R36 are R73 can be produced according to Production Process B.

[00807] It is also possible to produce the compound (1) using the other known coupling reaction in place of the Production Process B coupling reaction.

[00808] Production Process of the present tetrazolinone compound will be mentioned below.

[00809] The present tetrazolinone X compound can be produced, for example, by the following Production Processes.

(Synthesis Process A)

[00810] A compound represented by formula (BT1) (hereinafter referred to as compound (BT1)) can be produced according to the reaction mentioned in Production Process A, using a compound represented by formula (XO1) (hereinafter referred to as compound (XO1)) and a compound represented by the formula (XOT2) (hereinafter referred to as the compound (XOT2)):

[00811] where Z801 represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom, and R1, R2, R3, R4, R5, R6, R7, X, and Q are equal to defined above.

(Synthesis Process B)

[00812] The compound (BT1) can be produced according to the reaction mentioned in Production Process A, using the compound (A1) and a compound represented by the formula (XUT1) (hereinafter referred to as the compound (XUT1)):

[00813] in which the symbols are the same as defined above.

[00814] The process for synthesizing an intermediate compound will be mentioned in detail below.

(Reference Production Process A)

[00815] A compound represented by formula (XA3) (hereinafter referred to as compound (XA3)) can be produced by reacting a compound represented by formula (XA1) (hereinafter referred to as compound (XA1)) or a compound represented by (XA2 ) (hereinafter referred to as compound (XA2)) with an azidating agent:

[00816] where R1, R2, R3, R4, R5, R6, X, A, and Q are the same as defined above, R101 represents P11, P12, or P13, R91 represents a C1-C12 alkyl group, Z101 represents a chlorine atom or bromine atom, and the wavy line represents a binding site.

[00817] The reaction is usually carried out in a solvent.

[00818] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof.

[00819] Examples of the azidation agent to be used in the reaction include inorganic azides, such as sodium azide, barium azide, and lithium azide; and organic azides, such as trimethylsilyl azide and diphenylphosphoryl azide.

[00820] In the reaction, the azidation agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mol of the compound (XA1) or the compound (XA2).

[00821] The reaction temperature of the reaction is usually within a range of -20 to 150 'C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00822] If necessary, Lewis acid, such as aluminum chloride or zinc chloride can be added in the reaction, and these compounds are usually used in the proportion of 0.05 to 5 moles based on the 1 mol of the compound (XA1) or the compound (XA2).

[00823] After completion of the reaction, the compound (XA3) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound (XA3) can also be purified by chromatography, recrystallization, and the like.

(Reference B Production Process)

em que os símbolos são iguais ao definido acima.[00824] The compound (XA1) can be produced by reacting a compound represented by the formula (XB1) (hereinafter referred to as the compound (XB1)) with an isocyanating agent:

where the symbols are the same as defined above.

[00825] The reaction is usually carried out in a solvent.

[00826] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; esters, such as ethyl acetate and methyl acetate; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof.

[00827] Examples of the isocyanating agent to be used in the reaction include phosgene, diphosgene, triphosgene, thiophosgene, N, N-carbodiimidazole, and N, N-thiocarbodiimidazole.

[00828] In the reaction, the isocyanating agent is usually used in the proportion within a range of 0.34 to 10 moles based on the 1 mole of the compound (XB1).

[00829] The reaction temperature of the reaction is usually within a range of -20 to 150 ‘C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00830] If necessary, organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal hydrogen carbonates, such as sodium hydrogen carbonate can be added in the reaction, and these compounds are usually used in the proportion within a range of 0.05 to 5 moles based on the 1 mol of the compound (XB1 ).

[00831] After completion of the reaction, the compound (XA1) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound (XA1) can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference C Production Process)

em que os símbolos são iguais ao definido acima.[00832] The compound (XA2) can be produced by reacting a compound represented by the formula (XC1) (hereinafter referred to as the compound (XC1)) with a halogenating agent:

where the symbols are the same as defined above.

[00833] The reaction is usually carried out in a solvent.

[00834] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; esters, such as ethyl acetate and methyl acetate; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof.

[00835] Examples of the halogenating agent to be used in the reaction include phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, phosphorus oxybromide, phosphorus tribromide, phosphorus pentabromide, phosphorus triiodide, oxalyl dichloride oxalyl dibromide, triphosgene, diphosgene, phosgene, sulfuryl chloride, and the like.

[00836] In the reaction, the halogenating agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XC1).

[00837] The reaction temperature of the reaction is usually within a range of -20 to 15013. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

[00838] The catalyst can be added to the reaction and dimethylformamide is used. The catalyst is usually used in the proportion within a range of 0.001 to 1 mol based on the 1 mol of the compost (XC1).

[00839] If necessary, organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal hydrogen carbonates, such as sodium hydrogen carbonate, can be used in the reaction, and these compounds are usually used in proportion within a range of 0.05 to 5 moles based on the 1 mol of the compound (XC1 ).

[00840] After completion of the reaction, the compound (XA2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference D Production Process)

[00841] The compound (XA1) can be produced by reacting the compound (XB1) with a carbamation agent to obtain a compound represented by formula (XD1) (hereinafter referred to as the compound (XD1)), and then reacting the compound ( XD1) with an isocyanating agent:

[00842] where R3, R4, R5, R6, R101, and X are the same as defined above, and R111 represents a C1-C12 alkyl group or a phenyl group.

[00843] The process for producing the compound (XD1) from the compound (XB1) will be described below.

[00844] The reaction is usually carried out in a solvent.

[00845] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; Water; and mixtures thereof.

[00846] Examples of the carbamation agent to be used in the reaction include phenyl chlorocarbonate, methyl chlorocarbonate, ethyl chlorocarbonate, n-propyl chlorocarbonate, isopropyl chlorocarbonate, n-butyl chlorocarbonate, tert-butyl chlorocarbonate, di-tert-butyl dicarbonate, dimethyl dicarbonate, diethyl dicarbonate, O-phenyl chlorothioformate, O-methyl chlorothioformate, O-ethyl chlorothioform, and the like.

[00847] In the reaction, the carbamation agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XB1).

[00848] The reaction temperature of the reaction is usually within a range of -20 to ISO'S. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00849] If necessary, organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal hydrogen carbonates, such as sodium hydrogen carbonate, can be added to the reaction, and these compounds are usually used in the proportion within a range of 0.05 to 5 mol based on the 1 mol of the compound (XB1).

[00850] After completion of the reaction, the compound (XD1) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

[00851] The process for producing the compound (XA1) from the compound (XD1) will be described below.

[00852] The reaction is usually carried out in a solvent.

[00853] Examples of the solvent to be used in the reaction include ethers, such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, and methyl tert-butyl ether; aromatic hydrocarbons, such as toluene and xylene; halogenated hydrocarbons, such as carbon tetrachloride, chloroform or 1,2-dichloroethane, and chlorobenzene; nitriles, such as acetonitrile; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; and mixtures thereof.

[00854] Examples of the isocyanating agent to be used in the reaction include phosphorus pentachloride, phosphorus oxychloride, diphosphorus pentaoxide, trichlorosilane, dichlorosilane, monochlorosilane, boron trichloride, 2-chloro-1,3,2-benzodioxaborol, diiodosilane, methyltrichlorosilane, dimethyldichlorosilane, chlorotrimethylsilane, and the like.

[00855] In the reaction, the isocyanating agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XD1).

[00856] The reaction temperature of the reaction is usually within a range of -20 to 250 'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00857] If necessary, organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal hydrogen carbonates, such as sodium hydrogen carbonate can be added to the reaction, and these compounds are usually used in the proportion within a range of 0.05 to 5 moles based on the 1 mol of the compound (XD1 ).

[00858] After completion of the reaction, the compound (XA1) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference E Production Process)

[00859] A compound represented by the formula (XE2) (hereinafter referred to as the compound (XE2) can be produced by reacting a compound represented by the formula (XE1) (hereinafter referred to as the compound (XE1)) with hydrogen in the presence of a catalyst:

[00860] where R1, R2, R3, R4, R5, R6, A, and Q are the same as defined above, R181 represents a hydrogen atom or P21, and the wavy line represents a bonding site.

[00861] The reaction is usually carried out in a solvent.

[00862] Examples of the solvent to be used in the reaction include alcohols, such as methanol, ethanol, propanol, and butanol; esters, such as ethyl acetate, and butyl acetate; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; ethers, such as tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether, and diisopropyl ether; hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; Water; and mixtures thereof.

[00863] Examples of the catalyst to be used in the reaction include palladium support carbon (Pd / C), platinum support carbon (Pt / C), osmium support carbon (Os / C), ruthenium support carbon (Ru / C), rhodium support carbon (Rh / C), Raney nickel, and the like.

[00864] In the reaction, the catalyst is usually used in the proportion within a range of 0.0001 to 1 mol based on the 1 mol of the compound (XE1).

[00865] The reaction temperature of the reaction is usually within a range of -20 to IδO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00866] After completion of the reaction, the compound (XE2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference F Production Process)

[00867] The compound (XE2) can be produced by reacting the compound (XE1) with a reducing agent in the presence of an acid:

[00868] in which the symbols are the same as defined above.

[00869] The reaction is usually carried out in a solvent.

[00870] Examples of the solvent to be used in the reaction include aliphatic carboxylic acids, such as acetic acid; alcohols, such as methanol and ethanol; Water; and mixtures thereof.

[00871] Examples of the reducing agent to be used in the reaction include iron, tin, and zinc.

[00872] Examples of the acid to be used in the reaction include hydrochloric acid, sulfuric acid, acetic acid, an aqueous ammonium chloride solution, and the like.

[00873] In the reaction, the reducing agent is usually used in the proportion within a range of 1 to 30 moles based on the 1 mole of the compound (XE1).

[00874] The reaction temperature of the reaction is usually within a range of -20 to IδO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00875] After completion of the reaction, the compound (XE2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference G Production Process)

[00876] A compound represented by formula (XG2) (hereinafter referred to as compound (XG2)) can be produced by reacting a compound represented by formula (XG1) (hereinafter referred to as compound (XG1)) with compound (E1) in presence of a base:

[00877] where R3, R4, R5, R6, R7, X, and Z11 are the same as defined above, and R191 represents P11 or P12.

[00878] The reaction can be carried out according to the reaction mentioned in Production Process E.

(Reference H Production Process)

[00879] A compound represented by formula (XH2) (hereinafter referred to as compound (XH2)) can be produced by reacting a compound represented by formula (XH1) (hereinafter referred to as compound (XH1)) with a halogenating agent:

[00880] where R1, R2, R3, R4, R5, R6, R7, Z21, and X are the same as defined above, and R201 represents P51 or a nitro group.

[00881] The reaction is usually carried out in a solvent.

[00882] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, fluorobenzene, difluoro-robenzene, trifluorobenzene, chlorobenzene, dichlorobenzene, trichloro-benzene, α, α, trifluorol, α, trifluorol a, α-trichlorotoluene; esters, such as ethyl acetate and methyl acetate; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof.

[00883] Examples of the halogenating agent to be used in the reaction include a chlorinating agent, a brominating agent, or an iodizing agent, for example, chlorine, bromine, iodine, sulfuryl chloride, N-chlorosuccinimide, N- bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin, iodosuccinimide, tert-butyl hypochlorite, N-chloroglutarimide, N-bromoglutarimide, N-chloro-N-cyclohexyl-benzenesulfonimide, N-bromophthalimide, and the like.

[00884] It is also possible to use a radical initiator in the reaction.

[00885] Examples of the radical initiator to be used in the reaction include benzoyl peroxide, azobisisobutyronitrile (AIBN), diacyl peroxide, dialkyl peroxydicarbonate, tert-alkyl peroxyester, monoperoxycarbonate, di (tert-alkylperoxy) ketal and peroxide ketone, and the like.

[00886] In the reaction, the halogenating agent is usually used in the proportion within a range of 1 to 10 moles, and the radical initiator is usually used in the proportion within a range of 0.01 to 5 moles, based on 1 mol of the compound (XH1).

[00887] The reaction temperature of the reaction is usually within a range of -20 to 150 ‘C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00888] After completion of the reaction, the compound (XH2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference Production Process I)

[00889] A compound represented by the formula (XJ2) (hereinafter referred to as the compound (XJ2)) can be produced by reacting the compound (XH2) with a compound represented by the formula (XJ1) (hereinafter referred to as the compound (XJ1)):

[00890] where R1, R2, R3, R4, R5, R6, R201, R111, and Z21 are the same as defined above, and M represents sodium, potassium, or lithium.

[00891] The reaction is usually carried out in a solvent.

[00892] Examples of the solvent to be used in the reaction include ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; nitriles, such as acetonitrile; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, and butanol; and mixtures thereof.

[00893] Examples of the compound (XJ1) to be used in the reaction include sodium methoxide, sodium ethoxide, sodium n-propoxide, sodium n-butoxide, sodium isopropoxide, sodium sec-butoxide, sodium tert-butoxide , potassium methoxide, potassium ethoxide, potassium n-propoxide, potassium n-butoxide, potassium isopropoxide, potassium sec-butoxide, potassium tert-butoxide, sodium phenoxide, and the like.

[00894] In the reaction, the compound (XJ1) is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XH2).

[00895] The reaction temperature of the reaction is usually within a range of -20 to 150 ‘C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00896] After completion of the reaction, the compound (XJ2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference J Production Process)

em que os símbolos são iguais ao definido acima.[00897] A compound represented by the formula (XK1) (hereinafter referred to as the compound (XK1)) can be produced by reacting the compound (XH2) with water in the presence of a base:

where the symbols are the same as defined above.

[00898] The reaction is usually carried out in water, or a solvent containing water.

[00899] Examples of the solvent to be used in the reaction include ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; nitriles, such as acetonitrile; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, and butanol; and mixtures thereof.

[00900] Examples of the base to be used in the reaction include organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; organic metal acid salts, such as lithium formate, lithium acetate, sodium formate, sodium acetate, potassium formate, and potassium acetate; metal nitrates, such as silver nitrate and sodium nitrate; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates, such as sodium hydrogen carbonate; alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; and alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.

[00901] In the reaction, the base is usually used in the proportion within a range of 1 to 100 moles based on the 1 mole of the compound (XH2).

[00902] In the reaction, water is usually used in the proportion within a range of 1 mol to a large excess based on the 1 mol of the compound (XH2).

[00903] The reaction temperature of the reaction is usually within a range of -20 to 150 ^. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00904] After completion of the reaction, the compound (XK1) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference K Production Process)

em que os símbolos são iguais ao definido acima.[00905] The compound (XH2) can be produced by reacting the compound (XJ2) with a halogenating agent:

where the symbols are the same as defined above.

[00906] The reaction is usually carried out in a solvent.

[00907] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; organic acids, such as formic acid, acetic acid, and trifluoroacetic acid; Water; and mixtures thereof.

[00908] Examples of the halogenating agent to be used in the reaction include hydrochloric acid, hydrobromic acid, and hydroiodic acid.

[00909] In the reaction, the halogenating agent is usually used in the proportion within a range of 1 mol or more based on the 1 mol of the compound (XJ2).

[00910] The reaction temperature of the reaction is usually within a range of -20 to IδO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00911] After completion of the reaction, the compound (XH2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference L Production Process)

em que os símbolos são iguais ao definido acima.[00912] The compound (XH2) can be produced by reacting the compound (XK1) with a halogenating agent:

where the symbols are the same as defined above.

[00913] The reaction is usually carried out in a solvent.

[00914] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; esters, such as ethyl acetate and methyl acetate; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; organic acids, such as formic acid, acetic acid, and trifluoroacetic acid; Water; and mixtures thereof.

[00915] Examples of the halogenating agent to be used in the reaction include bromine, chlorine, sulfuryl chloride, hydrochloric acid, hydrobromic acid, hydroiodic acid, boron tribromide, phosphorus tribromide, trimethylsilyl chloride, trimethylsilyl bromide, trimethylsilyl iodide , thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, phosphorus oxybromide, phosphorus pentabromide, phosphorus triiodide, oxalyl dichloride, oxalyl dichromide, acetyl chloride, tetrabromide carbon, N-bromosuccinimide, lithium chloride, sodium iodide, acetyl bromide, and the like.

[00916] In the reaction, the halogenating agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XK1).

[00917] In order to accelerate the reaction, additives can be added according to the halogenating agent to be used, and specific examples thereof include zinc chloride for acetyl chloride, triphenylphosphine for carbon tetrabromide, sulfide for dimethyl for N-bromosuccinimide, boron trifluoride diethyl ether complex for sodium iodide, boron trifluoride diethyl ether complex for acetyl bromide, triethylamine and methanesulfonyl chloride for lithium chloride, aluminum chloride for sodium iodide, chloride from trimethylsilyl to sodium iodide, and the like. Any additives are usually used in proportion within a range of 0.01 to 5 moles based on the 1 mole of the compound (XK1).

[00918] The reaction temperature of the reaction is usually within a range of -20 to IδO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00919] After completion of the reaction, the compound (XH2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference M Production Process)

[00920] A compound represented by the formula (XM3) (hereinafter referred to as the compound (XM3)) can be produced by reacting the compound (XK1) with a compound represented by the formula (XM2) (hereinafter referred to as the compound (XM2)) in presence of a base:

[00921] wherein R1, R2, R3, R4, R5, R6, Z801, and R201 are the same as above, and R901 represents a C1-C6 alkyl group, a C1- C6 haloalkyl group, a C6-C16 group aryl, or a C6-C16 haloaryl group.

[00922] The reaction is usually carried out in a solvent.

[00923] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; nitriles, such as acetonitrile; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; and mixtures thereof.

[00924] Examples of the base to be used in the reaction include organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates, such as sodium hydrogen carbonate; alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal hydrides, such as lithium hydride, sodium hydride, and potassium hydride; alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.

[00925] In the reaction, the compound (XM2) is usually used in proportion within a range of 1 to 10 moles, and the base is usually used in proportion within a range of 1 to 5 moles, based on 1 mol of compound (XK1).

[00926] The reaction temperature of the reaction is usually within a range of -20 to IδO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00927] If necessary, sodium iodide, tetrabutylammonium iodide, and the like can be added in the reaction, and these compounds are usually used in the proportion within a range of 0.001 to 1.2 moles based on the 1 mole of the compound (XK1 ).

[00928] After completion of the reaction, the compound (XM3) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference N Production Process)

[00929] A compound represented by formula (XN12) (hereinafter referred to as compound (XN12)) can be produced according to the reaction mentioned in Production Process B, using a compound represented by formula (XN11) (hereinafter referred to as compound (XN11)) and compound (G21):

[00930] where R501 represents a hydrogen atom or an OR111 group, and R111, R1, R2, R4, R5, R6, R7, R71, X, Z31, and Z41 are the same as defined above.

em que os símbolos são iguais ao definido acima.[00931] A compound represented by formula (XN22) (hereinafter referred to as compound (XN22)) can be produced according to the reaction mentioned in Production Process B, using a compound represented by formula (XN21) (hereinafter referred to as compound (XN21)) and compound (G22):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00932] A compound represented by formula (XN32) (hereinafter referred to as compound (XN32)) can be produced according to the reaction mentioned in Production Process B, using a compound represented by formula (XN31) (hereinafter referred to as compound (XN31)) and compound (G22):

where the symbols are the same as defined above.

em que os símbolos são iguais ao definido acima.[00933] A compound represented by formula (XN42) (hereinafter referred to as compound (XN42)) can be produced according to the reaction mentioned in Production Process B, using a compound represented by formula (XN41) (hereinafter referred to as the compound (XN41)) and compound (G22):

where the symbols are the same as defined above.

[00934] The reaction can be performed according to the reaction mentioned in Production Process B.

em que os símbolos são iguais ao definido acima.[00935] According to the reaction mentioned in Production Process B, it is possible to produce a compound in which two or more substitutes selected from R3, R4, R5, and R6 are R71 or R72, among the group of compounds represented by formula (XN50):

where the symbols are the same as defined above.

[00936] In addition, the compound (XN50) can be produced using the other known coupling reaction in place of the coupling reaction mentioned in Production Process B.

(O Reference Production Process)

em que os símbolos são iguais ao definido acima.[00937] A compound represented by formula (XW2) (hereinafter referred to as compound (AXW2)) can be produced by reacting a compound represented by formula (XW1) (hereinafter referred to as compound (XW1)) with a compound represented by formula ( XW3) (hereinafter referred to as the compound (XW3)) in the presence of a reaction accelerator:

where the symbols are the same as defined above.

[00938] The reaction is usually carried out in a solvent.

[00939] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof, and the compound (XW3) can be used as the solvent.

[00940] Examples of the compound (XW3) to be used in the reaction include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, and sec-butyl alcohol.

[00941] Examples of the reaction accelerator to be used in the reaction include mineral acids, such as hydrochloric acid and sulfuric acid; carbodiimides, such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, and N '- (3-dimethylaminopropyl) -N-ethylcarbodiimide; organic acids, such as methanesulfonic acid and toluenesulfonic acid; Mitsunobu reaction reagents, such as diethyl azodicarboxylate / triphenylphosphine; thionyl chloride, boron-ethyl ether trifluoride complex, and the like.

[00942] In the reaction, a reaction accelerator is usually used in the proportion within a range of 0.01 to 10 moles based on the 1 mole of the compound (XW1).

[00943] If necessary, organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal hydrogen carbonates, such as sodium hydrogen carbonate can be added to the reaction, and these compounds are usually used in the proportion within a range of 0.01 to 5 moles based on the 1 mol of the compound (XW1 ).

[00944] In the reaction, an excess amount of the compound (XW3) is used based on the compound (XW1).

[00945] The reaction temperature of the reaction is usually within a range of -78 to WO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00946] After completion of the reaction, the compound (XW2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference P Production Process)

em que R3, R4, R5, R6, R91, e Z101 são iguais ao definido acima.[00947] The compound (XW2) can be produced by reacting the compound (XW1) with a halogenating agent to obtain a compound represented by formula (XV1) (hereinafter referred to as the compound (XV1)), and to react the compound ( XV1) with the compound (XW3):

where R3, R4, R5, R6, R91, and Z101 are the same as defined above.

[00948] The process for producing the compound (XV1) by reacting the compound (XW1) with a halogenating agent can be carried out according to the reaction mentioned in Reference Production Process C.

[00949] The process for producing the compound (XW2) from the compound (XV1) will be described below.

[00950] The reaction is usually carried out in a solvent.

[00951] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; and mixtures thereof, and the compound (XW3) can be used as the solvent.

[00952] Examples of the compound (XW3) to be used in the reaction include methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, and sec-butyl alcohol.

[00953] In the reaction, an excess amount of the compound (XW3) is used based on the compound (XV1).

[00954] The reaction temperature of the reaction is usually within a range of -78 to 100 'C. The reaction reaction time is usually within a range of 0.1 to 24 hours.

[00955] After completion of the reaction, the compound (XW2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Q Reference Production Process)

em que os símbolos são iguais ao definido acima.[00956] The compound (XW2) can be produced by reacting the compound (XW1) with an alkylating agent:

where the symbols are the same as defined above.

[00957] The reaction is usually carried out in a solvent.

[00958] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; esters, such as ethyl acetate and methyl acetate; sulfoxides, such as dimethyl sulfoxide; ketones, such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; nitriles, such as acetonitrile; Water; and mixtures thereof.

[00959] Examples of the alkylating agent to be used in the reaction include alkyl halides, such as diazomethane, trimethylsilyldiazomethane, chlorodifluoromethane, methyl bromide, ethyl bromide, n-propyl bromide, methyl iodide, ethyl iodide, n-propyl bromide, allyl bromide, cyclopropyl bromide, benzyl bromide, and 1,1-difluoro-2-iodoethane; dialkyl sulfates, such as dimethyl sulfate, diethyl sulfate, and di-n-propyl sulfate; and arylsulfonic acid or alkyl esters, such as methyl p-toluenesulfonate, ethyl p-toluenesulfonate, n-propyl p-toluenesulfonate, methyl methanesulfonate, ethyl methanesulfonate, and n-propyl methanesulfonate.

[00960] In the reaction, the alkylating agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XW1).

[00961] If necessary, organic bases, such as triethylamine, pyridine, N-methylmorpholine, 4-dimethylaminopyridine, diisopropylethylamine, and diazabicycloundecene; alkali metal carbonates, such as lithium carbonate, sodium carbonate, and potassium carbonate; alkali metal hydrogen carbonates, such as sodium hydrogen carbonate; and quaternary ammonium salts, such as tetra (n-butyl) ammonium hydroxide can be added in the reaction, and these compounds are usually used in proportion within a range of 0.01 to 5 moles based on the 1 mole of the compound ( XW1).

[00962] The reaction temperature of the reaction is usually within a range of -78 to WO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00963] After completion of the reaction, the compound (XW2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference R Production Process)

em que os símbolos são iguais ao definido acima.[00964] A compound represented by formula (XX2) (hereinafter referred to as compound (XX2)) can be produced by reacting a compound represented by formula (XX1) (hereinafter referred to as compound (XX1)) with a reducing agent:

where the symbols are the same as defined above.

[00965] The reaction is usually carried out in a solvent.

[00966] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; alcohols, such as methanol, ethanol, propanol, and butanol; Water; and mixtures thereof.

[00967] Examples of the reducing agent to be used in the reaction include lithium triethylborohydride, aluminum diisobutylhydride, lithium aminoborohydride, lithium borohydride, sodium borohydride, borane, a borane dimethyl sulfide complex, and a borane tetrahydrofuran complex.

[00968] In the reaction, the reducing agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XX1).

[00969] The reaction temperature of the reaction is usually within a range of -78 to WO'C. The reaction time of the reaction is usually within the range of 0.1 to 24 hours.

[00970] After completion of the reaction, the compound (XX2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference S Production Process)

em que os símbolos são iguais ao definido acima.[00971] A compound represented by formula (XZ2) (hereinafter referred to as compound (XZ2)) can be produced by reacting a compound represented by formula (XZ1) (hereinafter referred to as compound (XZ1)) with a reducing agent:

where the symbols are the same as defined above.

[00972] The reaction is usually carried out in a solvent.

[00973] Examples of the solvent to be used in the reaction include hydrocarbons, such as n-hexane, cyclohexane, toluene, and xylene; ethers, such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisol, methyl tert-butyl ether, and diisopropyl ether; halogenated hydrocarbons, such as chloroform, 1,2-dichloroethane, and chlorobenzene; acid amides, such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone; sulfoxides, such as dimethyl sulfoxide; nitriles, such as acetonitrile; alcohols, such as methanol, ethanol, propanol, and butanol; Water; and mixtures thereof.

[00974] Examples of the reducing agent to be used in the reaction include borane, a borane tetrahydrofuran complex, and a borane dimethyl sulfide complex. It is also possible to use borane to be generated by mixing a borohydride, such as sodium borohydride or potassium borohydride with an acid, such as sulfuric acid, hydrochloric acid, methanesulfonic acid, or a boron trifluoride diethyl ether complex.

[00975] In the reaction, the reducing agent is usually used in the proportion within a range of 1 to 10 moles based on the 1 mole of the compound (XZ1).

[00976] The reaction temperature of the reaction is usually within a range of -20 to WO'C. The reaction time of the reaction is usually within the range of 0.1 to 72 hours.

[00977] After completion of the reaction, the compound (XZ2) can be isolated by performing post-treatment operations, such as extracting the reaction mixture with an organic solvent, and drying and concentrating the organic layer. The isolated compound can also be purified by operations, such as distillation, chromatography, and recrystallization.

(Reference T Production Process)

em que os símbolos são iguais ao definido acima.[00978] A compound represented by formula (XS2) (hereinafter referred to as compound (XS2)) can be produced by reacting a compound represented by formula (XS1) (hereinafter referred to as compound (XS1)) with compound (A2) in presence of a base:

where the symbols are the same as defined above.

[00979] The reaction can be performed according to the reaction mentioned in Production Process A.

(U Reference Production Process)

em que os símbolos são iguais ao definido acima.[00980] A compound represented by formula (XU2) (hereinafter referred to as compound (XU2)) can be produced by submitting a compound represented by formula (XU1) (hereinafter referred to as compound (XU1)) and compound (B2) to a coupling reaction in the presence of a base and a catalyst:

where the symbols are the same as defined above.

[00981] The reaction can be carried out according to the reaction mentioned in Production Process B.

(Reference V Production Process)

em que os símbolos são iguais ao definido acima.[00982] The compound (B1) can be produced by reacting a compound represented by the formula (XO1) (hereinafter referred to as the compound (XO1)) with a compound represented by the formula (XO2) (hereinafter referred to as the compound (XO2)) in presence of a base:

where the symbols are the same as defined above.

[00983] The reaction can be carried out according to the reaction mentioned in Production Process A.

(Reference W Production Process)

em que os símbolos são iguais ao definido acima.[00984] The compound (B1) can be produced by reacting the compound (A1) with the compound (XU1) in the presence of a base:

where the symbols are the same as defined above.

[00985] The reaction can be carried out according to the reaction mentioned in Production Process A.

[00986] Although a form used for the present compound can properly be the present compound, the present compound is generally mixed with solid vehicles, liquid vehicles, surfactants, and the like, and optionally adding auxiliary agents for formulation, such as adherents, dispensers, and stabilizers for formulating in wetting powders, water-dispersible, flowable granules, dry fluids, emulsifiable concentrates, aqueous solutions, oily solutions, smoking agents, aerosols, microcapsules, and the like. In these formulations, the present compound is generally contained in a range of 0.1 to 99%, and preferably 0.2 to 90% by weight.

[00987] Examples of solid vehicles include clays (for example, kaolin, diatomaceous earth, synthetic hydrated silicon dioxide, Fubasami clay, bentonite, and acid clay), talc or other inorganic minerals (for example, sericite, quartz powder, powder sulfur, activated charcoal, calcium carbonate, and hydrated silica) in the form of fine or particulate powders, and examples of liquid vehicles include water, alcohols (for example, methanol and ethanol), ketones (for example, acetone and methyl ethyl ketone), aromatic hydrocarbons (for example, benzene, toluene, xylene, ethylbenzene, and methyl naphthalene), aliphatic hydrocarbons (for example, n-hexane, cyclohexane, and kerosene), esters (for example, ethyl acetate and butyl acetate ), nitriles (for example, acetonitrile and isobutyronitrile), ethers (for example, dioxane and diisopropylether), acid amides (for example, DMF and dimethylacetamide), and halogenated hydrocarbons (for example, dichloroethane, trichlorethylenone, and tetrachloride of carbon).

[00988] Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers, and polyoxyethylene compounds thereof, polyethylene glycol ethers, polyhydric alcohol esters, and alcohol derivatives sugar.

[00989] Examples of other auxiliary agents for formulation include adherents, dispensers and stabilizers, specifically casein, gelatin, polysaccharides (eg, starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, bentonite, sugars , water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinylpyrrolidone, and polyacrylic acids), PAP (acid isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or fatty acid esters thereof, and the like.

[00990] The method for applying the present control compound is not particularly limited, as long as the application form is a way in which the present compound can be applied substantially, and includes, for example, an application to plants, such as a foliage application; an application to the area to grow plants, such as a submerged treatment; and application to the soil, such as seed disinfection.

[00991] The present control agent can be used as a mixture with various oils or surfactants, such as mineral oils or vegetable oils. Specific examples of oils or surfactants, which can be used as a mixture with various oils or surfactants, include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), lharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundancell (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (trademark) registered), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark) ), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), BANOLE (registered trademark), and the like.

[00992] The present control agent can also be used as a mixture with or together with other fungicides, insecticides, acaricides, nematicides, and plant development regulators.

[00993] Examples of these other fungicides include the following:

[00994] (1) Azol Fungicides

[00995] such as propiconazole, protioconazole, triadimenol, proclorax, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, diphenoconazole, cyproconazole, metconazole, triflumizole, hexachonazole, trachyclonazole, trachyclonazole, trichyclonazole , imazalil, flutriafol, simeconazole, and ipconazole;

[00996] (2) Amine fungicides

[00997] such as fempropimorph, tridemorph, fempropidine, and spiroxamine;

[00998] (3) Benzimidazole fungicides

[00999] such as carbendazim, benomyl, thiabendazole, and thiophanate-methyl;

[001000] (4) Dicarboximide fungicides

[001001] such as procymidone, iprodione, and vinclozoline;

[001002] (5) Anilinopyridine fungicides

[001003] such as cyprodinil, pyrimethanil, and mepanipyrim;

[001004] (6) Phenylpyrrole fungicides

[001005] such as fempiclonil and fludioxonil;

[001006] (7) Strobilurin fungicides

[001007] such as cresoxim-methyl, azoxystrobin, trifloxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, dimoxystrobin, pyribenocarb, metominostrobin, orisastrobin, enestrobin, piraoxystrobin, pirametostrobin, pyrethoxystrobin, phloxyoxystrobin, phloxoxystrobin, phloxystrobin, phloxystrobin, phloxystrobin;

[001008] (8) Phenylamide fungicides

[001009] such as metalaxyl, metalaxyl-M or mefenoxam, benalaxyl, and benalaxyl-M or chiralaxyl;

[001010] (9) Carboxylic acid amide fungicides

[001011] such as dimetomorph, iprovalicarb, bentivalicarb-isopropyl, mandipropamide, and valifenal;

[001012] (10) Carboxamide fungicides

[001013] such as carboxine, mepronyl, flutolanyl, tifluzamide, fumametpir, boscalide, pentiopyrad, fluopyram, bixafen, pyrflufen, sexane, fluxpyroxade, isopyrazam, benzovindiflupir, isofetamide, 2- (3- acid amide [N- 4-difluorophenyl) phenyl] -3-trifluoromethylpyrazine-2-carboxylic acid, N- (1,1,3-trimethylindan-4-yl) -1-methyl-3-difluoromethylpyrazol-4-carboxylic acid amide (including racemate or enantiomer , a mixture of R form enantiomer and S form enantiomer in an optional relationship); and

[001014] (11) Other fungicides

[001015] such as dietofencarb, tiuram, fluazinam, mancozeb, chlorothalonil, captano, diclofluanide, folpet, quinoxifene, fenhexanide, phonoxadon, fenamidon, zoxamide, taboxam, amisulbrom, ciazofamide, flussenamide, flufenone, metrafenone, pyrphenone , fluopicolide, fosetil, cymoxanil, pencicurone, tolclofos-methyl, carproamide, diclocimet, phenoxanil, tricyclazole, pyroquilone, probenazole, isothianyl, thiadinyl, tebufloquine, clomezine, casugamycin, ferminzone, hydroquinone, validated iminoctadine, isoprothiolone, oxolinic acid, oxytetracycline, streptomycin, copper oxychloride, copper hydroxide, copper hydroxide sulfate, organocopper, sulfur, ametoctradine, fempyrazamine, oxathiaproline, 3-chloro-4- (2,6-difluorophenyl ) -6-methyl-5-phenylpyridazine, and 3-cyano-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine.

[001016] Examples of these other insecticides include:

[001017] (1) Organophosphorus compounds

[001018] such as Acephate, Aluminum Phosphide, Butathiophos, Cadaphos, Chlorethoxyphos, Chlorpheniphos, Chlorpyrifos, Chlorpyrifos-Methyl, Cyano-Phosphates: CYAP, Diazinone, Dichlorodiisopropyl Ether (DCIP), Diclofentiona: ECP, Dichlorides: DDV , dimethylvinfos, disulfotone, EPN, ethione, etoprofos, etrinfos, fentiona: MPP, phenitrothione: MEP, fostiazate, formothinone, hydrogen phosphide, isophenphos, isoxathione, malationa, messulfenes, metidationa: DMTP, monocrotosphos, monocrotos : ESP, parathione, fosalone, fosmetPMP, pirimiphos-methyl, pyridafentiona, quinalphos, fentoate: PAP, profenofos, propafos, protiofos, pirachlorfos, salitina, sulprofos, tebupirinfos, temefos, tetrachlorvinfos, terfufona, tertofufos, terfufona : DEP, vamidothione, forato, and cadusafos;

[001019] (2) Carbamate compounds

[001020] such as alanicarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloetocarb, ethiofencarb, feno-bucarb, phenothiocarb, phenoxycarb, furatiocarb, isoprocarb: MIPC, metolcarb, methanol, methacryl, pyromycin, methacryl, pyromycin, methacryl, pyromycin, methanol, - poxur: PHC, XMC, thiodicarb, xylylcarb, and aldicarb;

[001021] (3) Synthetic pyrethroid compounds

[001022] such as acrinatrine, alethrin, benflutrin, beta-cyfluthrin, bifentrin, cycloprotrin, cycloprotrin, cyhalothrin, cypermethrin, deltamethrin, sphenolerate, etofenprox, fempropatrin, fenvalerate, flucitrinate, fluvetrinate, fluofenprine, fluvetrin, fluflenetrinate , pralethrin, pyrethrins, resmethrin, sigma-cypermethrin, silafluofen, teflutrin, tralometrine, transflutrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, beta-cypermethrin, teta-cypermethrin, zeta-cipermetrine, keta-cypermethin, kinetin-ciperminthine , furamethrin, tau-fluvalinate, halfenprox, protrifenbute, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ) - (1 RS, 3RS; 1 RS, 3SR) -2,2-dimethyl-3 -prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ) - (1 RS, 3RS; 1 RS, 3SR) -2,2-dimethyl-3 prop-1-enylcyclopropanecarboxylate, and 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1 RS, 3RS; 1 RS, 3SR) -2,2-dimethyl-3- (2-methyl-1 - propenyl) cyclopropanecarboxylate;

[001023] (4) Nereistoxin Compounds

[001024] such as cartap, bensultap, thiocyclam, monosultap, and bis-sultap;

[001025] (5) Neonicotinoid Compounds

[001026] such as imidacloprid, nitempiram, acetamipride, thiamethoxam, thiacloprid, dinotefuran, and clothianidin;

[001027] (6) Benzoylurea Compounds

[001028] such as chlorfluazurone, bistriflurone, diafentiurone, diflu-benzurone, fluazurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, noviflumurone, teflubenzurone, triflumurone, and triflumurone, and triflumurone;

[001029] (7) Phenylpyrazole Compounds

[001030] such as acetoprol, etiprol, fipronil, vaniliprol, pyriprol, and pirafluprol;

[001031] (8) Bt toxin insecticides

[001032] such as live spores derived from crystal toxins produced from Bacillus thuringiesis, and a mixture thereof;

[001033] (9) Hydrazine Compounds

[001034] such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide;

[001035] (10) Organochlorine Compounds

[001036] such as aldrin, dieldrin, dienochlor, endosulfan, and methoxychlor;

[001037] (11) Natural insecticides

[001038] such as machine oil and nicotine sulfate; and

[001039] (12) Other insecticides

[001040] such as avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyromazine, 1,3-dichloropropene (DD), emamectin-benzoate, phenazaquin, flupirazophos, hydroprene, methoprene, indoxacarb, methoxicin-A, milbemycin, A pimetrozine, pyridalyl, pyriproxifene, spino-sad, sulfluramid, tolfempirade, triazamate, flubendiamide, doramectin, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulphide, chlordane, DDT, DSP, flufin - no, formethanate, metam-ammonium, metam-sodium, methyl bromide, potassium oil, spiromesifene, sulfur, metaflumizone, spirotetramate, pyrifluquinazone, espinetoram, chlorantraniliprol, cyantraniliprol, cyclaniliprol, sulfoxafurone, and flupir.

[001041] Examples of these other acaricides (acaricidally active ingredients) include acequinocyl, amitraz, benzoxide, biphenate, bromopropylate, quinomethionate, chlorobenzylate, chlorfensone (CPCBS), clofentezine, ciflumetophen, dicofol (celtane), tetoxazole, tetoxazole , phenothiocarb, fempiroxime, fluacripyrim, fluproxyphene, hexithazazox, propargite: BPPS, polynactins, pyridaben, pyrimidifene, tebufem-pirade, tetradifone, spirodiclofen, spiromesifene, spirotetrama, amidoflumet, and cienopene.

[001042] Examples of these other nematicides (nematitically active ingredients) include DCIP, phostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, imiciafos, fluensulfone, and the like.

[001043] Examples of these other plant development regulators include:

[001044] etefone, clormequat-chloride, mepiquat-chloride, gibberellin A typified by gibberellin A3, abscisic acid, kinetin, benzyladenine, 1,3-diphenylurea, forchlorphenurone, thidiazurone, 4-oxo-4- (2-phenylethyl) aminobutyric acid , Methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylate, 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylic acid, and the like.

[001045] The method for applying the present compound is not particularly limited, as long as the form of application is a way in which the present compound can be applied substantially, and includes, for example, an application to plants, such as an application of foliage; an application to the area to grow plants, such as a submerged treatment; and application to the soil, such as seed disinfection.

[001046] The application dose varies depending on the weather conditions, dosage forms, application time, application methods, areas to be applied, target diseases, target crops, and the like, and is usually within a range of 1 at 500 g, and preferably 2 to 200 g, per 1,000 m2 of the area to be applied. The emulsifiable concentrate, wetting powder, or suspension concentrate is usually applied by diluting with water. In this case, the concentration of the present compound after dilution is usually within the range of 0.0005 to 2% by weight, and preferably 0.005 to 1% by weight. The powder formulation or granular formulation is usually applied, like the one without dilution. In application to seeds, the amount of the present compound is usually within a range of 0.001 to 100 g, and preferably 0.01 to 50 g, per 1 kg of the seeds.

[001047] In the present invention, examples of the place where pests live include rice paddies, fields, tea gardens, orchards, non-agricultural land, houses, seed trays, seed boxes, seed soils, and seed beds.

[001048] Also, in another modality, for example, the present compound can be administered inside (inside the body) or outside (body surface) of the below mentioned vertebrate in order to exterminate systemically or non-systemically the living beings or parasites that are parasites in vertebrates. Examples of a method of internal administration include oral administration, anal administration, transplantation, administration via subcutaneous, intramuscular or intravenous injection. Examples of a method of external administration include transdermal administration. Also, the present compost can be ingested by a cattle, in order to exterminate sanitary insects that occur in the animal's excrement.

[001049] When the present compound is applied to animals, such as livestock and domestic animals on which pests are parasitic, the dose varies depending on the method of administration etc., and it is generally desired to administer the present compound so that the dose of the active ingredient (the present compound or salts thereof) is generally within a range of 0.1 mg to 2,000 mg, and preferably 0.5 mg to 1,000 mg, per 1 kg of the animal's body weight.

[001050] The present compound can be used as an agent for the control of plant diseases in agricultural areas, such as fields, rice fields, lawns, and orchards. The present compound can control diseases that occur in agricultural areas for the cultivation of the following "plants":

[001051] Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soy, peanuts, wheat, beet, rapeseed, sunflower, sugar cane, tobacco, and the like; Vegetables: olanaceous vegetables (for example, eggplant, tomatoes, peppers, pepper, and potatoes), cucumber vegetables (for example, cucumber, pumpkin, zucchini, watermelon, and melon), cruciferous vegetables (for example, Japanese radish, turnip white, horseradish, kohlrabi, chinese cabbage, cabbage, mustard leaf, broccoli, and cauliflower), asteraceous vegetables (for example, burdock, crown daisy, artichoke, and lettuce), lily vegetables (for example, green onions, onions, garlic, and asparagus), starchy vegetables (for example, carrots, parsley, celery, and parsnips), kenopodiaceous vegetables (for example, spinach and chard), llamaaceous vegetables (for example, Perilla fruits-cens, mint , and basil), strawberry, sweet potato, Japanese Dioscorea, colocasia, and the like.

[001052] Flowers:

[001053] Ornamental foliage plants:

[001054] Fruits: pomegranate fruits (for example, apple, pear, Japanese pear, Chinese quince, and quince), stone fruits (for example, peach, plum, nectarine, Prunus mume, cherry fruit, apricot, and prune ), citrus fruits (eg Mikan, orange, lemon, lime, grapefruit), nuts (eg chestnut, walnuts, hazelnuts, almonds, pistachios, cashews, and macadamia nuts), berries (eg , blueberry, cranberry, blackberry, and Raspberry), grape, persimmon persimmon, olive, Japanese plum, banana, coffee, date, coconut, and the like;

[001055] Non-fruit trees: tea, mulberry, flowering plant, trees on the road (eg ash, birch, dogwood, Eucalyptus, Ginkgo biloba, cashew fruit, maple, Quercus, poplar, Judas tree , Liquidambar formosana, maple, zelkova, Japanese tuia, fir wood, hemlock, juniper, Pinus, Picea, and Taxus cuspidate) ', and the like.

[001056] The "plants" mentioned above include genetically modified crops.

[001057] Pests that can be controlled by the present compound include plant pathogens, such as filamentous fungus, as well as harmful arthropods, such as harmful insects and harmful mites, and nematelmints, such as nematodes, and specifically include the following examples, however, they are not limited to them.

[001058] Rice diseases: blast (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), sheath rust (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), and velvety mold (Scleophophora macrospora) ', wheat diseases: powdery mold (Erysiphe graminis), fusarium rust (Fusarium gaminaarum, F. avenaceum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondndita), snow mold {Micronectriella nivale), ferrugem typhulasnow {Ty sp.), loose rust (Ustilago tritici), smelly rust (Tilletia caries, T. controversa), ocelo (Pseudocercosporella herpotrichoides), leaf spot (Septoria tritici), glume spot (Stagonospora nodorum), brown spot {Pirenophora tritici- repentis ), rust from seeding caused by bacteria of the genus {Rhizoctonia solani), and include all diseases (Gaeumannomyces graminis) ', Barly diseases. powdery mold (Erysiphe graminis), fusarium rust (Fusarium gaminaarum, F. avenaceum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei), loose rust (Ustilago nuda), yellowing {Rhynchospo- rium secalis), reticular spot (Pirenophora teres), helminthosporiosis (Cochliobolus sativus), leaf stripe (Pirenophora graminaa), Ramularia disease (Ramularia collo-cygni), and seed rust caused by bacteria of the genus (Rhizoctonia solaniy corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polisora), northern leaf rust (Setosphaeria turcica), southern leaf rust (Chliobolus heterostrophus), anthracnose (Colletotrichum gfaminicola), gray leaf spot (Cercospora zea maydis), ocelo (Kabatiella zeae), and leaf spot phaeosphaeria (Phaeosphaeria maydis) ', cotton diseases: anthracnose (Colletotrichum gossypii), gray mold (Ramuraria areola), and leaf spot alternaria (Alternaria macrospo- ra, A. gossypii) ', coffee diseases: rust (Hemileia vastatrixy rape diseases: sclerotin rot (Sclerotinia sclerotiorum), black spot (Alternaria brassicae), and black leg (Phoma lingam)', citrus diseases: melanosis (Diaporthe citri ), scabies (Elsinoe fawcetti), and fruit rot (Penicillium digitatum, P. italicumy apple diseases: flowering rust (Monilinia malí), cancer (Waltz ceratosperm), powdery mold (Podosphaera leucotricha), leaf spot alternaria (Alternaria alternata apple pathotype), scabies (Venturia inae-qualis), and bitter rot (Glomerella cingulata, Colletotrichum acutatuum) ', pear diseases: scabies (Venturia nashicola, V. pirina), black spot (Alternaria alternata Japanese pear pathotype), and rust (Gymnosporangium haraeanumy diseases of the peach: brown rot (Monilinia fructicola), mange (Cladosporium carpophilum), and Phomopsis rot (Phomopsis sp.); grape diseases: anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata, Colletotrichum acutatum), powdery mold (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), and velvety mold (Plasm); Japanese persimmon diseases: anthracnose (Gloeosporium kaki) and leaf spot (Cercospora kaki, Mycosphaerella nawae) ', diseases of the gourd family: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem rust , target spot (Corynespora cassiicola), fusariosis (Fusarium oxisporum), velvety mold (Pseudoperonospora cubensis), phytophthora rot (Phytophthora sp.), and withering (Pythium sp.); tomato diseases: early rust (Alternaria solani), leaf mold (Cladosporium fulvum), leaf mold (Pseudocercospora fuligena), and late rust (Phytophthora infestans) ', Eggplant diseases: brown spot (Phomopsis vexans) and mold pulverento (Erysiphe cichoracearum) ', cruciferous vegetable diseases: alternaria leaf spot (Alternaria japonica), white spot (Cercosporella brassicae), cruciferous hernia (Plasmodiophora parasitica), and velvety mold (Peronospora parasitica)', diseases of the Welsh onion: rust (Puccinia allii) ', soybean diseases: purple spot (Cercospora kikuchii), sphaceloma scad (Elsinoe glycines), pod rust and stem (Diaporthe phaseolorum var .oyae), rust (phakopsora pachyrhizi), target spot ( Corynes-pora cassiicola), anthracnose (Colletotrithum glycines, C. truncatum), Rhizoctonia aerial rust (Rhizoctonia solani), brown septoria spot (Septoria glycines), and frog eye leaf spot (Cercospora sojina) ', fei diseases common: anthracnose (Colletotrichum linemtianum) ', peanut diseases: early leaf spot (Cercospora personata), late leaf spot (Cercospora arachidicola), and southern rust (Sclerotium rolfsii)', garden pea diseases: powdery mold (Erysiphe pisi) ', potato diseases: early rust (Alternaria solani), late rust (Phytophthora infestans), and wilt of verticillium (verticillium albo-atrum, V. dahliae, V. nigres-cens); strawberry diseases: powdery mold (Sphaerotheca humuli) ', tea plant diseases: liquid bubble rust (Exobasidium reticulatum), white mange (Elsinoe leucospila), gray rust (Pesta- lotiopsis sp.), and anthracnose (Colletotrichum theae-sinensis) ', tobacco diseases: brown spot (Alternaria longipes), powdery mold (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), velvety mold (Peronospora tabacina), and black stem (Phytophthora nicoti- anae)', diseases of the sugar beet: cercosporiosis (Cercospora beticola), leaf rust (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), and root rot of aphanomyces (Aphanomyces sochlioides) ', diseases of the rose: black spot (Diplo- carpon rosae) and powdery mold (Sphaerotheca pannosa) ', chrysanthemum diseases: leaf rust (Septoria chrysanthemi-indici) and white pustule (Puccinia horiana)', onion diseases: botrytis leaf rust (Botrytis cinerea, B. byssoidea, B. squamosa ), gray mold neck rot (Botrytis slli), and small rot rot (Botrytis squamosa) ', various crop diseases: gray mold (Botrytis cinerea) and sclerotia rot (Sclerotinia sclerotiorum)', Japanese radish diseases: alternaria leaf spot (Alternaria brassicicola) ', Lawn diseases: dollar spot (Sclerotinia homeocarpa) and brown spot and large spot (Rhizoctonia solani)', and banana diseases: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).

[001059] Hemiptera: plant hoppers (Delphacidae), such as small brown plant hopper (Laodelphax striatellus), brown rice hopper (Nilaparvata lugens), and white rice hopper (Sogatella furcifera) ', spittlebugs (Deltocephalidae) , such as green rice hopper (Nephotettix cincticeps) and green rice hopper (Nephotettix virescens) ', aphids (Aphididae), such as cotton aphid (Aphis gossypii), green peach aphid (Myzus persicae), cabbage aphid ( Brevicoryne brassicae), potato aphid (Macrosiphum euphorbiae), foxglove aphid (Aulacorthum solani), oat cherry-bird aphid (Rhopalosiphum padi), and tropical citrus aphid (Toxoptera citricidus) ', stink bugs (Penta- tomee) such as green stink bug (Nezara antennata), bean bug (Riptortus clavetus), rice bug (Leptocoris chinensis), white spotted bug (Eysarco risis parvus), stink bug (Hal mixed yomorpha), and spotted plant stink (Lygus lineolarisy, white flies (Aleyrodidae), such as greenhouse whitefly (Trialeurodes vaporariorum) and silver leaf whitefly (Bemisia argentifolii) ', mealybugs (Coccidae), such such as California Red Cochineal (Aonidiella aurantii), San José Cochineal (Comstockaspis perniciosa), northern citrus cochineal (Unaspis citri), red wax cochineal (Ceroplastes rubens), and cotton pad cochineal (Icerya purchasi) ', bed bugs cord (Tingidae) ', jumping plant lice (Homoptera, Psylloidea)', and bedbugs (Cimex lectularius).

[001060] Lepidoptera: piralid moths (Piralidae), such as rice stem borer (Chilo suppressalis), yellow rice borer (Tryporyza incertulas), rice leaf furler (Cnaphalocrocis medinalis), cotton leaf furler (Notarcha derogata ), Indian meal moth (Plodia interpunctella), oriental corn borer (Ostrinia furnacalis), cabbage web caterpillar (Hellula undalis), and field grass web (Pediasia teterrellus) ', owl moths (Noctuidae), such as common caterpillar (Spodoptera litura), beet caterpillar (Spodoptera exigua), cereal caterpillar (Pseudaletia separata), cabbage caterpillar (Mamestra brassicae), black caterpillar (Agrotis ipsilon), beet semi-launcher ( Plusia nigrisigna), Thoricoplusia spp., Heliothis spp., And Helicoverpa spp .; white butterflies (Pieridae), such as common white (Pieris rapae) ', tortricid moths (Tortricidae), such as Adoxophyes spp., oriental fruit moth (Grapholita molesta), soybean pod borer (Leguminivora glycinivorella) , bean pod caterpillar (Matsumuraeses azukivora), summer fruit tortrix (Adoxophyes orana fasciata), minor tea tortrix (Adoxophyes sp.), oriental tea tortrix (Homona magnanima), apple tortrix (Archips fuscocupreanus), and small moth (Cydia pomonel- / a); leaf spot miners (Gracillariidae), such as tea leaf winder (Caloptilia theivora), and apple leaf miner (Phyllonorycter ringoneella); leaf miners (Gracillariidae), such as tea leaf winder (Caloptilia theivora) and apple leaf miner (Phyllonorycter ringoneella) ', small moths (Carposimidae), such as peach moths (Carposina niponensis)', moths lyonetiid (Lyonetiidae), such as Lyonetia spp .; Toucan moths (Lymantriidae), such as Lymantria spp. and Euproctis spp .; yponomeutid moths (Yponomeutidae), such as diamond-shaped backs (Plutella xylostella); gelechild moths (Gelechiidae), such as pink caterpillar (Pectinophora gossypiella) and potato caterpillar (Phthorimaea operculella) ', tiger and allied moths (Arctiidae), such as autumn webworm (Hyphantria cunea) \ and tineid moths (Tineidine moths) , such as moth for casemaking clothes (Tinea translu- cens), and moth for clothes of strong fabric (Tineola bisselliella).

[001061] Tisanopterans: yellow citrus thrips (Frankliniella occidentalis), melon thrips (Thrips palmi), yellow tea thrips (Scirotothrips dorsalis), onion thrips (Thrips tabaci), flower thrips (Frankliniella intonsa) , and tobacco thrips (Frankliniella fusca).

[001062] Diptera: houseflies (Musca domestica), common mosquito (Culex pipiens pallens), blowfly (Tabanus trigonus), onion larva (Hylemya anitgua), corn seed larva (Hylemya platura), Anopheles sinensis, miner of rice leaf (Agromyza oryzae), rice leaf miner (Hidrellia griseola), rice stem larva (Clorops oryzae), melon fly (Dacus cucurbitatae), Mediterranean fruit fly (Ceratitis capitata), and miner of the leaf of the vegetable (Liriomyza trifolii).

[001063] Coleoptera: twenty-eight-spot ladybug (Epilachna vigintioctopunctata), cucurbit leaf beetle (Aulacophora femo-ralis), yellow-striped flea beetle (Phyllotreta striolata), rice leaf beetle (Oulema oryzae), weevil rice (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), weevil (Anthonomus grandis), azuki bean weevil (Callosobru- chus chinensis), hunting bug (Sfenophorus venatus), Japanese beetle (Popillia japonica), cupric beetle Anomalous cuprea), corn root (Diabrotica spp.), Colorado potato beetle (Leptinotarsa decemlineata), click beetles (Agriotes spp.), Cigarette beetle (Lasioderma serricorne), varied carper beetle (Anthrenus verbasci), beetle red flour (Tribolium castaneum), dust-fixing beetle (Lyctus brunneus), white-spotted long-horned beetle (Anoplophora malasiaca), and pine shoot beetle (Tomicus piniperda).

[001064] Orthopterans: Asian grasshoppers (Locusta migrativa), African soft cricket (Gryllotalpa africana), rice grasshopper (Ox / a yezoensis), and rice grasshopper (Oxia japonica).

[001065] Hymenoptera: cabbage stalks (Athalia rosae), leaf-cutting ants (Acromyrmex spp.), And fire ants (Solenopsis spp.).

[001066] Nematodes: white tip nematode (Aphelenchoides besseyi), strawberry sprout nematode (Nothotylenchus acris), soybean cyst nematode (Heterodera glycines), southern root knot nematode (Meloidogyne incognita), nematode of the incognita lesion of the cobb root (Pratylenchus penetrans), and nematode of the false root node (Na-cobbus aberrans).

[001067] Blattariae: German cockroach (Blattella germanica), smoky brown cockroach (Periplaneta fuliginosa), American cockroach (Periplaneeta America), brown cockroach (Periplaneta brunnea), and oriental cockroach (Eastern Blatta is).

[001068] Mites: Tetranychidae (for example, two-spotted spider mite (Tetranychus urticae), red citrus mite (Ponyonychus citri), and Oligonychus spp.); Eryophyidae (for example, pink citrus rust mite (Aculops pelekassi)) ', Tarsonemidae (for example, white mite (Poliphagotarsonemus latus)); Tenuipalpidae, Tuckerellidae ', Tuckerellidae Acaridae (for example, common grain mite (Tyrophagus putrescentiae))', Pyroglyphidae (for example, American household dust mite (Dermatophagoides farinae) and domestic dust mite (Dermatophausides-) chetrs) ' tidae (for example, cheyletid mite (Cheyletus eruditus), Cheyletus malaccensis, and Cheyletus moorer, and Dermanyssidae.

[001069] The formulation comprising the present compound or salts thereof can be used in the field with respect to a treatment of livestock diseases and products industry for livestock, and can exterminate living beings or parasites that are parasitic. cos inside and / or outside vertebrates, such as humans, cows, sheep, pigs, poultry, dog, cat, and fish, in order to maintain public health. Examples of pests include ticks (Ixodesspp.) (For example, Ixodes scapularis), Boophilus spp. (for example, bovine tick (Boophilus microplus)), Amblyomma spp., Hyalomma spp., Rhipicephalus spp. (for example, kennel tick (Rhipicephalus sanguineus)), Haemaphysalis spp. (for example, Haemaphysalis longicornis), dermacentor spp., Ornithodoros spp. (eg Ornithodoros moubata), red mite (Dermahyssus gallinae), phantom ant (Ornithonyssus sylviarum), Sarcoptes spp. (for example, Sarcoptes scabiei), Psoroptes spp., Chorioptes spp., Demodexxpp., Eutrombicula spp., Ades spp. (for example, Asian tiger mosquito (Aedes albopictus)), Anophelesspp., Culex spp., Culicodes spp., Muscaspp., Hypoderma spp., Gasterophilus spp., Haematobia spp., Tabanus spp., Simulium spp., Triatoma spp. , lice (Phthirapter) (for example, Damalinia spp.), Linognathus spp., Haematopinus spp., Ctenocephalides spp. (for example, cat flea (Ctenocephalides felis)) Xenosylla spp., Pharaoh's ant (monomorium pharaonis) and nematodes [for example, hairy worm (for example, Nippostrongylus brasiliensis, Trichostrongylus axei, Trichostrongylus colubriin formis), . (for example, Trichinella spiriralis), barber's pole worm (Haemonchus contortus), Nematodirus spp. (for example, Nematodirus battus), Ostertagia circumcincta, Cooperia spp., Hyminolepis nana, and the like.

EXAMPLES

[001070] The present invention will be described in greater detail below by means of Production Examples, Formulation Examples, and Test Examples, however the present invention is not limited to these Examples.

[001071] First, the Production Examples will be described.

Production Example 1

[001072] A mixture of 0.40 g of AA1 mentioned in Synthesis Example 1, 0.19 g of phenylboronic acid, 0.68 g of tripotassium phosphate, 0.10 ml of water, 0.09 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium (ll) dichloromethane addition product, and 5 ml of dioxane were stirred with heating under reflux for 6 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.32 g of 1-methyl-4- [3-methyl-2- (6-phenylpyridin-2-yloxymethyl) phenyl] -1,4- dihydrotetrazol-5-one (hereinafter referred to as the present compound 1).

[001073] In the same way as in Production Example 1, the present compounds 2 to 205 were synthesized.

[Tabela 2]

[Tabela 3]

[Tabela 4]

[Tabela 5]

[Tabela 6]

[Tabela 7]

[Tabela 8]

[Tabela 9]

[Tabela 10]

[Tabela 11]

[Tabela 12]

[Tabela 13]

[Tabela 14]

[Tabela 15]

Tabela 16]

Tabela 17]

Tabela 18]

Tabela 19]

Tabela 20]

[Tabela 21]

[Tabela 22]

Tabela 23]

Tabela 24]

Tabela 25]

Tabela 26]

[Tabela 27]

Tabela 28]

Tabela 29]

Tabela 30]

Tabela 31]

Tabela 32]

Tabela 33]

Tabela 34]

[Tabela 35]

Tabela 36]

Tabela 37]

Tabela 38]

Tabela 39]

[001074] The structural formulas of the present compounds and the 1H NMR data of them are shown in Table 1 to Table 39. [Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

[Table 14]

[Table 15]

Table 16]

Table 17]

Table 18]

Table 19]

Table 20]

[Table 21]

[Table 22]

Table 23]

Table 24]

Table 25]

Table 26]

[Table 27]

Table 28]

Table 29]

Table 30]

Table 31]

Table 32]

Table 33]

Table 34]

[Table 35]

Table 36]

Table 37]

Table 38]

Table 39]

Production Example 160

[001083] A mixture of 0.51 g of AA1 mentioned in Synthesis Example 1, 0.41 g of 1-methylpiperazine, 0.38 g of potassium carbonate, and 5 ml of N, N-dimethylformamide was stirred at IδO 'C for 15 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.38 g of 1-methyl-4- {3-methyl-2- [2- (4-methylpiperazin-1 -yl) -pyridin- 6-yloxymethyl] phenyl} -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 160).

[001084] 1H-NMR (CDCl3) δ (ppm): 7.40-7.35 (3H, m), 7.25-7.22 (1H, m), 6.15 (1H, d, J = 8.2 Hz), 6.01 (1H, d, J = 7.7 Hz), 5.30 (2H, s), 3.62 (3H, s), 3.50 (4H, t, J = 5.1 Hz), 2.52 (4H, t, J = 5.1 Hz), 2.49 (3H, s), 2.35 (3H, s).

Production Example 161

[001085] A mixture of 0.49 g of AA1 mentioned in Synthesis Example 1, 0.34 g of morpholine, 0.36 g of potassium carbonate, and 4 ml of N, N-dimethylformamide was stirred at 130 ° C for 15 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.21 g of 1-methyl-4- [3-methyl-2- (2-morpholin-4-yl-pyridin-6-) iloxymethyl) phenyl] -1,4-dihydrotetrazole-5-one (hereinafter referred to as the present compound 161).

[001086] 1H-NMR (CDCl3) δ (ppm): 7.41-7.37 (3H, m), 7.26-7.23 (1H, m), 6.13 (1H, d, J = 7.8 Hz), 6.05 (1H, d, J = 8.0 Hz), 5.30 (2H, s), 3.81 (4H, t, J = 4.6 Hz), 3.62 (3H, s), 3.44 (4H, t, J = 4.6 Hz), 2.48 (3H, s).

Production Example 162

[001087] A mixture of 0.50 g of AA1 mentioned in Synthesis Example 1, 0.34 g of piperidine, 0.37 g of potassium carbonate, and 5 ml of N, N-dimethylformamide was stirred at 120 ° C for 10 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.41 g of 1-methyl-4- [3-methyl-2- (2-piperidin-1-yl-pyridin-6-yloxymethyl) -phenyl] -1,4-dihydrotetrazole-5-one (hereinafter referred to as the present compound 162).

[001088] 1H-NMR (CDCl3) õ (ppm): 7.40-7.36 (2H, m), 7.34 (1H, t, J = 8.0 Hz), 7.26-7.21 (1H, m), 6.15 (1H, d, J = 8.0 Hz), 5.94 (1H, d, J = 8.0 Hz), 5.30 (2H, s), 3.62 (3H, s), 3.48-3.46 (4H, m), 2.49 (3H, s), 1.63 (6H, brs).

Production Example 206

[001089] A mixture of 0.20 g of AA1 mentioned in Synthesis Example 1, 0.11 g of pyrazole, 0.18 g of potassium tert-butoxide, and 5 ml of dimethyl sulfoxide was stirred at 100 ° C for 2 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.09 g of 1-methyl-4- {3-methyl-2- [2- (1 H-pyrazol-1-yl) - pyridin -6-yloxymethyl] -phenyl} -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 206).

[001090] 1H-NMR (CDCl3) δ (ppm): 8.46-8.44 (1H, m), 7.73-7.72 (1H, m), 7.66-7.64 (1H, m), 7.52 (1H, d, J = 7.8 Hz), 7.41-7.40 (2H, m), 7.27-7.25 (1H, m), 6.55 (1H , dd, J = 8.0, 0.7 Hz), 6.46 - 6.45 (1H, m), 5.45 (2H, s), 3.53 (3H, s), 2.53 ( 3H, s).

Production Example 207

[001091] A mixture of 0.20 g of AA1 mentioned in Synthesis Example 1, 0.15 g of 3,5-dimethyl-1H-pyrazole, 0.18 g of potassium tert-butoxide, and 5 ml of sulfoxide of dimethyl was stirred at 100 ° C for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.05 g of 1-methyl-4- {3-methyl-2- [2- (3,5-dimethyl-1 H-pyrazole- 1 -i I) pyridin-6-ioxymethyl] phenyl} -1,4-dihydrotetrazole-5-one (hereinafter referred to as the present compound 207).

[001092] 1H-NMR (CDCl3) δ (ppm): 7.67-7.63 (1H, m), 7.45-7.41 (3H, m), 7.28-7.26 (1H, m), 6.54 (1H, d, J = 8.2 Hz), 6.00 (1H, s), 5.33 (2H, s), 3.56 (3H, s), 2.66 ( 3H, s), 2.50 (3H, s), 2.30 (3H, s).

Production Example 163

[001093] A mixture of 0.30 g of CA25 mentioned in Reference Production Example 25, 0.16 g of 2-chloro-5-methoxypyrimidine, 0.45 g of tripotassium phosphate, 1.00 ml of water, 0.06 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium (11) dichloromethane addition product, and 10 ml of dimethoxyethane was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.10 g of 1- {2- [3- (5-methoxypyrimidin-2-yl) phenoxymethyl] -3-methylphenyl} -4-methyl -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 163).

[001094] 1H-NMR (CDCl3) δ (ppm): 8.47 (2H, s), 7.96 (1H, dt, J = 7.7, 1.2 Hz), 7.91-7.90 (1H, m), 7.45-7.40 (2H, m), 7.36 (1H, t, J = 7.9 Hz), 7.29 (1H, dd, J = 6.7, 2 , 4 Hz), 6.96-6.93 (1H, m), 5.13 (2H, s), 3.97 (3H, s), 3.62 (3H, s), 2.52 (3H , s).

Production Example 164

[001095] A mixture of 0.30 g of CA25 mentioned in Reference Production Example 25, 0.12 g of 2-chloropyridine, 0.45 g of tripotassium phosphate, 1.00 ml of water, 0.06 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium (11) dichloromethane addition product, and 10 ml of dimethoxyethane was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.10 g of 1-methyl-4- [3-methyl-2- (3-pyridin-2-yl-phenoxymethyl) phenyl] -1 , 4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 164).

[001096] 1H-NMR (CDCl3) δ (ppm): 8.69-8.67 (1H, m), 7.77-7.69 (2H, m), 7.57-7.55 (2H, m), 7.44-7.22 (5H, m), 6.95-6.92 (1H, m), 5.11 (2H, s), 3.60 (3H, s), 2.51 (3H, s).

Production Example 165

[001097] A mixture of 0.30 g of CA25 mentioned in Reference Production Example 25, 0.16 g of 3-chloro-6-methoxypyridazine, 0.45 g of tripotassium phosphate, 1.00 ml of water, 0.06 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium (11) dichloromethane addition product, and 10 ml of dimethoxyethane was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.23 g of 1- {2- [3- (3-methoxypyridazin-6-yl) phenoxymethyl] -3-methylphenyl} -4-methyl -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 165).

[001098] 1H-NMR (CDCh) δ (ppm): 7.77 (1H, d, J = 9.4 Hz), 7.64- 7.63 (1H, m), 7.56-7.54 (1H, m), 7.45-7.36 (3H, m), 7.30-7.28 (1H, m), 7.05 (1H, d, J = 9.2 Hz), 6, 98-6.95 (1H, m), 5.11 (2H, s), 4.19 (3H, s), 3.61 (3H, s), 2.51 (3H, s).

[001099] In the same way as in Production Examples 163, 164, and 165, the present compounds 208 to 214 were synthesized.

[001100] The structural formulas of the present compounds and 1H NMR data are shown in Table 40. [Table 40]

Production Example 215

[001101] A mixture of 0.3 g of CA29 mentioned in Reference Production Example 30, 0.28 g of 4-bromo-1-methyl-1H-pyrazole, 0.37 g of tripotassium phosphate, 0.5 ml of water, 0.07 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium (11) dichloromethane addition product, and 5 ml of dimethoxyethane was stirred with heating under reflux for 2 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.07 g of 1-methyl-4- {3-methyl-2- [6- (1-methyl-1 H-pyrazol-4- il) pyridin-2-yloxymethyl] -phenyl} -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 215).

[001102] 1H-NMR (CDCh) δ (ppm): 7.89 (1H, s), 7.87 (1H, s), 7.51-7.47 (1H, m), 7.39-7 , 38 (2H, m), 7.25-7.23 (1H, m), 7.01 (1H, d, J = 7.3 Hz), 6.47 (1H, d, J = 8.0 Hz), 5.45 (2H, s), 3.95 (3H, s), 3.53 (3H, s), 2.53 (3H, s).

[001103] In the same manner as in Production Example 215, the present compounds 216 to 221 were synthesized.

[001104] The structural formulas of the present compounds and 1H NMR data are shown in Table 41. [Table 41]

[001105] Next, with respect to the production of the present tetrazolinone X composition, Synthesis Examples are shown.

Synthesis Example 1

[001106] To a mixture of 4.68 g of CA20 mentioned in Reference Production Example 20 and 100 ml of tetrahydrofuran, 1.02 g of 55% sodium hydride were added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, 5.03 g of 2,6-dibromopyridine were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 13 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 6.99 g of 1- [2- (2-bromopyridin-6-yloxymethyl) -3-methylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one (referred to as AA1).

[001107] 1H-NMR (CDCh) δ (ppm): 7.41-7.35 (3H, m), 7.25-7.23 (1H, m), 7.03 (1H, d, J = 7.3 Hz), 6.59 (1H, d, J = 8.2 Hz), 5.39 (2H, s), 3.69 (3H, s), 2.56 (3H, s).

Synthesis Example 2

[001108] To a mixture of 2.72 g of CA22 mentioned in Reference Production Example 22 and 50 ml of tetrahydrofuran, 0.53 g of 55% sodium hydride were added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, 2.62 g of 2,6-dibromopyridine was added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 4 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.96 g of 1- [2- (2-bromopyridin-6-yloxymethyl) -3-cyclopropylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001109] 1H-NMR (CDCh) δ (ppm): 7.43-7.36 (2H, m), 7.26-7.23 (2H, m), 7.04 (1H, dd, J = 7.4, 0.6 Hz), 6.60 (1H, dd, J = 8.2, 0.6 Hz), 5.59 (2H, s), 3.68 (3H, s), 2, 28-2.21 (1H, m), 1.04-0.99 (2H, m), 0.79-0.75 (2H, m).

Synthesis Example 3

[001110] To a mixture of 2.58 g of CA21 mentioned in Reference Production Example 21 and 50 ml of tetrahydrofuran, 0.53 g of 55% sodium hydride were added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, 2.61 g of 2,6-dibromopyridine was added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 4 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 3.64 g of 1- [2- (2-bromopyridin-6-yloxymethyl) -3-ethylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001111] 1H-NMR (CDCh) δ (ppm): 7.47-7.42 (2H, m), 7.38 (1H, t, J = 7.8 Hz), 7.26-7.24 (1H, m), 7.04 (1H, d, J = 7.2 Hz), 6.59 (1H, d, J = 8.2 Hz), 5.39 (2H, s), 3.68 (3H, s), 2.91 (2H, q, J = 7.6 Hz), 1.29 (3H, t, J = 7.6 Hz).

Synthesis Example 4

[001112] To a mixture of 2.00 g of CA24 mentioned in Reference Production Example 24 and 40 ml of tetrahydrofuran, 0.40 g of 55% sodium hydride was added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, 1.97 g of 2,6-dibromopyridine was added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 12 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.92 g of 1- [2- (2-bromopyridin-6-yloxymethyl) -3-chlorophenyl] - 4-methyl-1,4- dihydrotetrazol-5-one.

[001113] 1H-NMR (CDCh) δ (ppm): 7.61 (1H, dd, J = 8.2, 1.2 Hz), 7.46 (1H, t, J = 8.0 Hz), 7.41-7.35 (2H, m), 7.05 (1H, d, J = 7.5 Hz), 6.60 (1H, d, J = 8.0 Hz), 5.54 (2H , s), 3.68 (3H, s).

Synthesis Example 5

[001114] To a mixture of 2.00 g of CA23 mentioned in Reference Production Example 23 and 40 ml of tetrahydrofuran, 0.41 g of 55% sodium hydride was added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, 2.00 g of 2,6-dibromopyridine were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 12 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.93 g of 1- [2- (2-bromopyridin-6-yloxymethyl) -3-methoxyphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001115] 1H-NMR (CDCh) δ (ppm): 7.46 (1H, t, J = 8.2 Hz), 7.36 (1H, t, J = 7.8 Hz), 7.09 ( 1H, d, J = 8.0 Hz), 7.05-7.01 (2H, m), 6.57 (1H, d, J = 8.2 Hz), 5.46 (2H, s), 3.93 (3H, s), 3.66 (3H, s).

Synthesis Example 6

[001116] To a mixture of 1.54 g of CA20 mentioned in Reference Production Example 20 and 35 ml of tetrahydrofuran, 0.34 g of 55% sodium hydride was added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, 1.04 g of 4,6-dichloropyrimidine were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.13 g of 1- [2- (4-chloropyrimidin-6-yloxymethyl) -3-methylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001117] 1H-NMR (CDCh) δ (ppm): 8.48 (1H, s), 7.44-7.38 (2H, m), 7.27-7.25 (1H, m), 6 , 69 (1H, s), 5.45 (2H, s), 3.71 (3H, s), 2.53 (3H, s).

Synthesis Example 7

[001118] To a mixture of 1.54 g of CA20 mentioned in Reference Production Example 20 and 35 ml of N, N-dimethylformamide, 0.34 g of 55% sodium hydride were added under cooling, followed by stirring. for 30 minutes. To the reaction mixture, 1.04 g of 2,6-dichloropyrazine were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.17 g of 1- [2- (2-chloropyrazin-6-yloxymethyl) -3-methylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001119] 1H-NMR (CDCh) δ (ppm): 8.13 (1H, s), 8.04 (1H, s), 7.44- 7.39 (2H, m), 7.30-7 , 26 (1H, m), 5.43 (2H, s), 3.71 (3H, s), 2.56 (3H, s).

Synthesis Example 8

[001120] To a mixture of 1.23 g of CA20 mentioned in Reference Production Example 20, 0.98 g of 4-bromo-2-fluoropyridine, and 10 ml of tetrahydrofuran, 0.63 g of tert- potassium butoxide was added under cooling, followed by stirring for 30 minutes. The temperature of the reaction mixture was raised to room temperature, followed by stirring for 30 minutes. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.86 g of 1- [2- (4-bromopyridin-2-yloxymethyl) -3-methylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001121] 1H-NMR (CDCh) δ (ppm): 7.88 (1H, d, J = 5.6 Hz), 7.41- 7.36 (2H, m), 7.26-7.23 (1H, m), 6.99 (1H, dd, J = 5.6, 1.7 Hz), 6.86 (1H, d, J = 1.7 Hz), 5.36 (2H, s) , 3.69 (3H, s), 2.53 (3H, s).

Synthesis Example 9

[001122] A mixture of 2.99 g of CA7 mentioned in Reference Production Example 7, 1.87 g of 5-bromo-2-methylphenol, 2.76 g of potassium carbonate, and 40 ml of acetonitrile was stirred with heating under reflux for 2 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 3.49 g of 1- [2- (3-bromo-6-methylphenoxymethyl) -3-methoxyphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001123] 1H-NMR (CDCl3) δ (ppm): 7.47 (1H, t, J = 8.1 Hz), 7.10-7.03 (3H, m), 6.95-6.89 (2H, m), 5.25 (2H, s), 3.95 (3H, s), 3.63 (3H, s), 1.92 (3H, s).

Synthesis Example 10

[001124] A mixture of 7.00 g of CA14 mentioned in Reference Production Example 14, 4.49 g of 3-bromophenol, 4.44 g of potassium carbonate, and 100 ml of acetonitrile was stirred with heating under reflux for 3 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 8.22 g of 1- [2- (3-bromophenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazole- 5-one.

[001125] 1H-NMR (CDCl3) δ (ppm): 7.45-7.39 (2H, m), 7.28 (1H, dd, J = 7.2, 1.9 Hz), 7.15 -7.03 (3H, m), 6.80 (1H, dt, J = 7.6, 1.9 Hz), 5.00 (2H, s), 3.64 (3H, s), 2, 48 (3H, s).

Synthesis Example 11

[001126] To a mixture of 2.83 g of CA14 mentioned in Reference Production Example 14 and 50 ml of N, N-dimethylformamide, 0.48 g of 55% sodium hydride was added under cooling, followed by stirring. for 30 minutes. To the reaction mixture, 1.91 g of 5-bromopyridin-3-ol was added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 20 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.81 g of 1- [2- (3-bromopyridin-5-yloxymethyl) -3-methylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001127] 1H-NMR (CDCl3) δ (ppm): 8.31 (1H, d, J = 1.9 Hz), 8.20 (1H, d, J = 2.4 Hz), 7.48- 7.41 (2H, m), 7.36-7.35 (1H, m), 7.30 (1H, dd, J = 7.4, 1.6 Hz), 5.06 (2H, s) , 3.67 (3H, s), 2.49 (3H, s).

Synthesis Example 12

[001128] To a mixture of 5.66 g of CA14 mentioned in Reference Production Example 14 and 100 ml of N, N-dimethylformamide, 0.96 g of 55% sodium hydride were added under cooling, followed by stirring. for 30 minutes. To the reaction mixture, 2.84 g of 2-chloropyridin-4-ol were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 24 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 5.10 g of 1- [2- (2-chloropyridin-4-yloxymethyl) -3-methylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001129] 1H-NMR (CDCl3) δ (ppm): 8.19 (1H, d, J = 5.7 Hz), 7.48- 7.41 (2H, m), 7.31 (1H, dd , J = 7.6, 1.1 Hz), 6.84 (1H, d, J = 2.3 Hz), 6.73 (1H, dd, J = 5.7, 2.3 Hz), 5 , 07 (2H, s), 3.66 (3H, s), 2.48 (3H, s).

Synthesis Example 13

[001130] To a mixture of 2.64 g of CA20 mentioned in Reference Production Example 20 and 60 ml of tetrahydrofuran, 0.58 g of 55% sodium hydride were added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, under cooling, 1.79 g of 2,4-dichloropyrimidins were added. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.62 g of 1 - [2- (2-chloropyrimidin-4-yloxymethyl) -3-methylphenyl] - 4-methyl-1,4- dihydrotetrazol-5-one and 1.43 g of 1- [2- (4-chloropyrimidin-2-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one.

[001131] 1 - [2- (2-C loropi ri mid i n-4-i loxy methyl I) -3-methyl Ifenyl] -4-methyl I-1,4-dihydrotetrazol-5-one

[001132] 1H-NMR (CDCl3) δ (ppm): 8.26 (1H, d, J = 5.7 Hz), 7.45- 7.39 (2H, m), 7.28-7.26 (1H, m), 6.59 (1H, d, J = 5.7 Hz), 5.48 (2H, s), 3.72 (3H, s), 2.56 (3H, s).

[001133] 1 - [2- (4-C loropi ri mid i n-2-i loxy methyl I) -3-methyl Ifenyl] -4-methyl I-1,4-dihydrotetrazol-5-one

[001134] 1H-NMR (CDCl3) δ (ppm): 8.28 (1H, d, J = 5.3 Hz), 7.41- 7.36 (2H, m), 7.27-7.24 (1H, m), 6.93 (1H, d, J = 5.3 Hz), 5.48 (2H, s), 3.73 (3H, s), 2.59 (3H, s).

Synthesis Example 14

[001135] To a mixture of 2.64 g of CA20 mentioned in Reference Production Example 20 and 60 ml of tetrahydrofuran, 0.58 g of 55% sodium hydride were added under cooling, followed by stirring for 30 minutes. minutes. To the reaction mixture, 1.80 g of 2,4-dichloro-1,3,5-triazine were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 12 hours and further stirring at 50 ° C for 4 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.24 g of 1- [2- (4-chloro-1,3,5-triazin-2-yloxymethyl) -3-methylphenyl] - 4-methyl-1,4-dihydrotetrazol-5-one.

[001136] 1H-NMR (CDCl3) δ (ppm): 8.64 (1H, s), 7.46-7.37 (2H, m), 7.29-7.27 (1H, m), 5 , 56 (2H, s), 3.74 (3H, s), 2.58 (3H, s).

Synthesis Example 15

[001137] A mixture of 1.48 g of CA14 mentioned in Reference Production Example 14, 1.00 g of 3-bromo-2-fluorophenol, 1.08 g of potassium carbonate, and 30 ml of acetonitrile was stirred with heating under reflux for 3 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.9 g of 1- [2- (3-bromo-2-fluorophenoxymethyl) -3-methylphenyl] -4-methyl- 1,4- dihydrotetrazol-5-one.

[001138] 1H-NMR (CDCl3) δ (ppm): 7.44-7.39 (2H, m), 7.31-7.26 (1H, m), 7.16-7.12 (1H, m), 6.93-6.85 (2H, m), 5.12 (2H, s), 3.68 (3H, s), 2.52 (3H, s).

Synthesis Example 16

[001139] A mixture of 7.20 g of CA14 mentioned in Reference Production Example 14, 5.00 g of 3-bromo-4-methylphenol, 5.30 g of potassium carbonate, and 150 ml of acetonitrile was stirred with heating under reflux for 5 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 10.1 g of 1- [2- (3-bromo-4-methylphenoxymethyl) -3-methylphenyl] -4-methyl- 1,4- dihydrotetrazol-5-one.

[001140] 1H-NMR (CDCh) δ (ppm): 7.44-7.38 (2H, m), 7.30-7.26 (1H, m), 7.11-7.07 (2H, m), 6.72 (1H, dd, J = 8.4, 2.6 Hz), 4.97 (2H, s), 3.65 (3H, s), 2.48 (3H, s), 2.31 (3H, s).

Synthesis Example 17

[001141] A mixture of 1.30 g of CA14 mentioned in Reference Production Example 14, 1.00 g of 5-bromo-2-chlorophenol, 0.95 g of potassium carbonate, and 30 ml of acetonitrile was stirred with heating under reflux for 5 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.60 g of 1- [2- (5-bromo-2-chlorophenoxymethyl) -3-methylphenyl] -4-methyl- 1,4- dihydrotetrazol-5-one.

[001142] 1H-NMR (CDCl3) δ (ppm): 7.45-7.39 (2H, m), 7.31-7.29 (1H, m), 7.19-7.17 (1H, m), 7.05-7.02 (2H, m), 5.13 (2H, s), 3.68 (3H, s), 2.53 (3H, s).

Synthesis Example 18

[001143] A mixture of 7.06 g of CA14 mentioned in Reference Production Example 14, 5.00 g of 5-bromo-2-fluorophenol, 5.16 g of potassium carbonate, and 150 ml of acetonitrile was stirred with heating under reflux for 5 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 10.0 g of 1- [2- (5-bromo-2-fluorophenoxymethyl) -3-methylphenyl] -4-methyl-1,4- dihydrotetrazol-5-one.

[001144] 1H-NMR (CDCl3) δ (ppm): 7.45-7.38 (2H, m), 7.28 (1H, dd, J = 7.3, 1.8 Hz), 7.08 -7.02 (2H, m), 6.92 (1H, dd, J = 10.8, 8.7 Hz), 5.09 (2H, s), 3.68 (3H, s), 2, 52 (3H, s).

Synthesis Example 19

[001145] A mixture of 6.64 g of CA14 mentioned in Reference Production Example 14, 5.00 g of 3-bromo-4-methoxyphenol, 4.87 g of potassium carbonate, and 100 ml of acetonitrile was stirred with heating under reflux for 5 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 9.17 g of 1- [2- (3-bromo-4-methoxyphenoxymethyl) -3-methylphenyl] -4-methyl- 1,4- dihydrotetrazol-5-one.

[001146] 1H-NMR (CDCl3) δ (ppm): 7.45-7.38 (2H, m), 7.28-7.26 (1H, m), 7.11-7.10 (1H, m), 6.83-6.76 (2H, m), 4.96 (2H, s), 3.83 (3H, s), 3.65 (3H, s), 2.48 (3H, s ).

Synthesis Example 20

[001147] A mixture of 1.44 g of CA14 mentioned in Reference Production Example 14, 1.00 g of 3-bromo-5-methylphenol, 1.06 g of potassium carbonate, and 30 ml of acetonitrile was stirred with heating under reflux for 5 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.80 g of 1- [2- (3-bromo-5-methylphenoxymethyl) -3-methylphenyl] -4-methyl- 1,4- d i-hydrotetrazol-5-one.

[001148] 1H-NMR (CDCl3) δ (ppm): 7.45-7.38 (2H, m), 7.31-7.26 (1H, m), 6.93 (1H, br s), 6.84-6.83 (1H, m), 6.61 (1H, br s), 4.97 (2H, s), 3.65 (3H, s), 2.48 (3H, s), 2.28 (3H, s).

Synthesis Example 21

[001149] A mixture of 7.06 g of CA14 mentioned in Reference Production Example 14, 5.00 g of 3-bromo-4-fluorophenol, 5.16 g of potassium carbonate, and 150 ml of acetonitrile was stirred with heating under reflux for 5 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 9.93 g of 1- [2- (3-bromo-4-fluorophenoxymethyl) -3-methylphenyl] -4-methyl- 1,4- dihydrotetrazol-5-one.

[001150] 1H-NMR (CDCh) δ (ppm): 7.45-7.39 (2H, m), 7.29-7.27 (1H, m), 7.06-6.99 (2H, m), 6.78-6.74 (1H, m), 4.97 (2H, s), 3.65 (3H, s), 2.48 (3H, s).

[001151] Regarding the production of intermediates to produce the present compounds mentioned above, Reference Production Examples will be shown below.

Reference Production Example 1

[001152] Anhydrous aluminum chloride (21.9 g) was added to 250 ml of N, N-dimethylformamide under cooling, followed by stirring for 15 minutes. To this was added 10.7 g of sodium azide and the mixture was stirred for 15 minutes, followed by the addition of 25.0 g of 1-chloro-3-isocyanate-2-methylbenzene and also heating at 80 ° C for 5 hours. After cooling, the reaction solution was added to a mixture of 35 g of sodium nitrite, 2 L of water, and 500 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 17.0 g of 1- (2-methyl-3-chlorophenyl) -1,4- dihydrotetrazol-5-one (referred to as CA1).

[001153] 1H-NMR (CDCl3) δ (ppm): 2.32 (3H, s), 7.28-7.36 (2H, m), 7.57 (1H, dd, J = 6.8, 2.2 Hz), 13.08 (1H, s).

Reference Production Example 2

[001154] To a mixture of 10.00 g of CA1 mentioned in Reference Production Example 1 and 100 ml of N, N-dimethylformamide, 2.30 g of 60% sodium hydride were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. To the reaction mixture, 3.2 ml of methyl iodide was added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.56 g of 1- (2-methyl-3-chlorophenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA2).

[001155] 1H-NMR (CDCl3) δ (ppm): 2.30 (3H, s), 3.73 (3H, s), 7.27 (1H, d, J = 2.7 Hz), 7, 28 (1H, d, J = 7.1 Hz), 7.52 (1H, dd, J = 2.7, 6.8 Hz).

Reference Production Example 3

[001156] A mixture of 1.56 g of CA2 mentioned in Reference Production Example 2, 0.34 g of 1,1'-azobis (cyclohexane-1-carbonitrile), 1.42 g of N-bromosuccinimide , and 30 ml of chlorobenzene was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 1.94 g of 1- (2-bromomethyl-3-chlorophenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA3).

[001157] 1H-NMR (CDCl3) δ (ppm): 3.76 (3H, s), 4.69 (2H, s), 7.35 (1H, dd, J = 1.2, 8.1 Hz ), 7.43 (1H, t, J = 8.1 Hz), 7.58 (1H, dd, J = 1.2, 8.1 Hz).

Reference Production Example 4

[001158] A mixture of 15.0 g of 3-amino-1-methoxy-2-methylbenzene, 48.7 g of triphosgene, and 350 ml of toluene was stirred with heating under reflux for 3 hours. After resting to cool, the reaction mixture was concentrated under reduced pressure to obtain 17.0 g of 1-methoxy-3-isocyanate-2-methylbenzene (referred to as CA4).

[001159] 1H-NMR (CDCl3) δ (ppm): 2.19 (3H, s), 3.82 (3H, s), 6.69 (1H, d, J = 8.2 Hz), 6, 72 (1H, dd, J = 0.5, 8.0 Hz), 7.09 (1H, t, J = 8.2 Hz).

Reference Production Example 5

[001160] Anhydrous aluminum chloride (16.0 g) was added to 180 ml of N, N-dimethylformamide under cooling, followed by stirring for 15 minutes. To this was added 7.8 g of sodium azide and the mixture was stirred for 15 minutes, followed by the addition of 17.0 g of CA4 mentioned in Reference Production Example 4 and also heating at 80 ° C for 4.5 hours. After cooling, the reaction solution was added to a mixture of 25 g of sodium nitrite, 2 L of water, and 500 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 16.2 g of 1- (2-methyl-3-methoxyphenyl) -1,4- dihydrotetrazol-5-one (referred to as CA5).

[001161] 1H-NMR (DMSO-dβ) δ (ppm): 1.99 (3H, s), 3.87 (3H, s), 7.01 (1H, d, J = 8.1 Hz), 7.17 (1H, d, J = 8.1 Hz). 7.36 (1H, t, J = 8.3 Hz), 14.63 (1H, s).

Reference Production Example 6

[001162] To a mixture of 10.00 g of CA5 mentioned in Reference Production Example 5 and 100 ml of N, N-dimethylformamide, 2.47 g of 60% sodium hydride were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 1 hour. To the reaction mixture, 3.5 ml of methyl iodide was added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.19 g of 1- (2-methyl-3-methoxyphenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA6).

[001163] 1H-NMR (CDCl3) δ (ppm): 2.11 (3H, s), 3.72 (3H, s), 3.88 (3H, s), 6.95 (1H, d, J = 8.2 Hz), 6.98 (1H, d, J = 8.5 Hz), 7.29 (1H, t, J = 8.2 Hz).

Reference Production Example 7

[001164] A mixture of 2.19 g of CA6 mentioned in Reference Production Example 6, 0.52 g of 1,1'-azobis (cyclohexane-1-carbonitrile), 2.16 g of N-bromosuccinimide , and 40 ml of chlorobenzene was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 2.36 g of 1- (2-bromomethyl-3-methoxyphenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA7).

[001165] 1H-NMR (CDCl3) δ (ppm): 3.74 (3H, s), 3.96 (3H, s), 4.93 (2H, s), 7.02 (1H, dd, J = 1.0, 8.5 Hz), 7.04 (1H, d, J = 9.0 Hz), 7.43 (1H, t, J = 8.1 Hz).

Reference Production Example 8

[001166] A mixture of 25.0 g of 1-bromo-2-methyl-3-aminobenzene, 60.0 g of triphosgene, and 400 ml of toluene was stirred with heating under reflux for 3 hours. After resting to cool, the reaction mixture was concentrated under reduced pressure to obtain 30.3 g of 1-bromo-3-isocyanate-2-methylbenzene (referred to as CA8).

[001167] 1H-NMR (CDCl3) δ (ppm): 2.42 (3H, s), 7.00 (1H, dt, J = 0.5, 8.0 Hz), 7.05 (1H, dd , J = 1.7, 8.0 Hz), 7.39 (1H, dd, 1.5, 7.7 Hz).

Reference Production Example 9

[001168] Anhydrous aluminum chloride (19.7 g) was added to 220 ml of N, N-dimethylformamide under cooling, followed by stirring for 15 minutes. To this was added 9.6 g of sodium azide and the mixture was stirred for 15 minutes, followed by the addition of 30.3 g of CA8 mentioned in Reference Production Example 8 and also heating at 80 ° C for 5 hours. After cooling, the reaction solution was added to a mixture of 33 g of sodium nitrite, 2 L of water, and 500 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 31.4 g of 1- (2-methyl-3-bromophenyl) -1,4- dihydrotetrazol-5-one (referred to as CA9).

[001169] 1H-NMR (DMSO-d6) δ (ppm): 2.22 (3H, s), 7.34 (1H, t, J = 7.2 Hz), 7.49 (1H, dd, J = 8.2, 1.1 Hz), 7.82 (1H, dd, J = 8.0, 1.0 Hz), 14.72 (1H, s).

Reference Production Example 10

[001170] To a mixture of 31.4 g of CA9 mentioned in Reference Production Example 9 and 250 ml of N, N-dimethylformamide, 5.90 g of 60% sodium hydride were added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 1 hour. To the reaction mixture, 8.4 ml of methyl iodide was added under cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 8.47 g of 1- (2-methyl-3-bromophenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA10).

[001171] 1H-NMR (CDCh) δ (ppm): 2.33 (3H, s), 3.73 (3H, s), 7.21 (1H, dt, J = 0.5, 7.8 Hz ), 7.30 (1H, dd, J = 1.0, 8.0 Hz), 7.71 (1H, dd, J = 1.2, 8.3 Hz).

Reference Production Example 11

[001172] A mixture of 8.47 g of CA10 mentioned in Reference Production Example 10, 1.54 g of 1,1'-azobis (cyclohexane-1-carbonitrile), 6.44 g of N-bromosuccinimide , and 125 ml of chlorobenzene was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 7.52 g of 1- (2-bromomethyl-3-bromophenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA11).

[001173] 1H-NMR (CDCh) δ (ppm): 3.76 (3H, s), 4.71 (2H, s), 7.34 (1H, t, J = 7.8 Hz), 7, 38 (1H, dd, J = 8.0, 1.7 Hz), 7.77 (1H, dd, J = 7.8, 1.7 Hz).

Reference Production Example 12

[001174] A mixture of 45.0 g of CA11 mentioned in Reference Production Example 11, 37.4 g of sodium methoxide, and 600 ml of tetrahydrofuran was stirred at room temperature for 3 hours. Saturated sodium bicarbonate water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 36.2 g of 1- (2-methoxymethyl-3-bromophenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA12) were obtained.

[001175] 1H-NMR (CDCl3) δ (ppm): 3.23 (3H, s), 3.72 (3H, s), 4.67 (2H, s), 7.33 (1H, t, J = 7.8 Hz), 7.38 (1H, dd, J = 1.2, 8.1 Hz), 7.76 (1H, dd, J = 1.5, 7.8 Hz).

Reference Production Example 13

[001176] A mixture of 36.2 g of CA12 mentioned in Reference Production Example 12, 23.2 g of methylboronic acid, 66.7 g of cesium fluoride, 10.6 g of dichloride dichloride addition product of [1,1'-bis (diphenylphosphino) ferrocene] palladium (ll), and 500 ml of dioxane was stirred at 90 ° C for 5.5 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 25.6 g of 1- (2-methoxymethyl-3-methylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA13).

[001177] 1H-NMR (CDCl3) δ (ppm): 2.48 (3H, s), 3.23 (3H, s), 3.72 (3H, s), 4.42 (2H, s), 7.21 (1H, t, J = 5.1 Hz), 7.35 (2H, d, J = 4.8 Hz).

Reference Production Example 14

[001178] A mixture of 25.6 g of CA13 mentioned in Reference Production Example 13, 50 ml of acetic acid, and 50 ml of a 25% acetic acid-hydrogen bromide solution was stirred at 65 <C for 1 hour. A saturated saline solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 27.9 g of 1- (2-bromomethyl-3-methylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA14) were obtained.

[001179] 1H-NMR (CDCl3) δ (ppm): 2.51 (3H, s), 3.75 (3H, s), 4.51 (2H, s), 7.22-7.24 (1H , m), 7.36-7.39 (2H, m).

Reference Production Example 15

[001180] A mixture of 30.1 g of CA12 mentioned in Reference Production Example 12, 12.9 g of cyclopropylboronic acid, 46.2 g of cesium fluoride, 8.2 g of dichloride dichloride addition product of [1,1'-bis (diphenylphosphino) ferrocene] palladium (ll), and 680 ml of dioxane was stirred at 90 ° C for 4 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 26.0 g of 1- (2-methoxymethyl-3-cyclopropylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA15).

[001181] 1H-NMR (CDCh) δ (ppm): 7.36 (1H, t, J = 8.0 Hz), 7.20 (2H, d, J = 8.0 Hz), 4.64 ( 2H, s), 3.72 (3H, s), 3.24 (3H, s), 2.20-2.13 (1H, m), 1.04-1.00 (2H, m), 0 , 76-0.72 (2H, m).

Reference Production Example 16

[001182] A mixture of 26.0 g of CA15 mentioned in Reference Production Example 15, 40 ml of acetic acid, and 40 ml of a 25% acetic acid-hydrogen bromide solution was stirred at 65 'C for 2 hours. A saturated saline solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 30.8 g of 1- (2-bromomethyl-3-cyclopropylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA16) were obtained.

[001183] 1H-NMR (CDCh) δ (ppm): 7.38 (1H, t, J = 7.8 Hz), 7.26-7.22 (2H, m), 4.77 (2H, s ), 3.75 (3H, s), 2.16-2.09 (1H, m), 1.10-1.06 (2H, m), 0.82-0.78 (2H, m).

Reference Production Example 17

[001184] A mixture of 29.8 g of CA12 mentioned in Reference Production Example 12, 35.2 g of tributylvinyl tin, 11.6 g of tetracistriphenylphosphinapalladium, and 500 ml of toluene was stirred under reflux for 14 hours. After cooling, a saturated aqueous ammonium chloride solution was poured into a reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 19.7 g of 1- (2-methoxymethyl-3-ethenylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA17).

[001185] 1H-NMR (CDCl3) δ (ppm): 7.67 (1H, dd, J = 7.8, 1.3 Hz), 7.44 (1H, t, J = 7.8 Hz), 7.29 (1H, dd, J = 7.8, 1.3 Hz), 7.11 (1H, dd, J = 17.4, 11.1 Hz), 5.72 (1H, dd, J = 17.4, 1.3 Hz), 5.44 (1H, dd, J = 11.1, 1.3 Hz), 4.45 (2H, s), 3.72 (3H, s), 3, 23 (3H, s).

Reference Production Example 18

[001186] A mixture of 19.7 g of CA17 mentioned in Reference Production Example 17, 3.02 g of a palladium-fibroin composite, and 1 L of methanol was stirred in a hydrogen atmosphere at room temperature for 11 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 19.3 g of 1- (2-methoxymethyl-3-ethylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one ( referred to as CA18).

[001187] 1H-NMR (CDCl3) δ (ppm): 7.42-7.38 (2H, m), 7.23-7.20 (1H, m), 4.44 (2H, s), 3 , 72 (3H, s), 3.22 (3H, s), 2.82 (2H, q, J = 7.6 Hz), 1.27 (3H, t, J = 7.6 Hz).

Reference Production Example 19

[001188] A mixture of 19.3 g of CA18 mentioned in Reference Production Example 18, 40 ml of acetic acid, and 40 ml of a 25% acetic acid-hydrogen bromide solution was stirred at βδ'C for 1.5 hours. A saturated saline solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate water and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 23.3 g of 1- (2-bromomethyl-3-ethylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA19) were obtained.

[001189] 1H-NMR (CDCl3) δ (ppm): 7.44-7.37 (2H, m), 7.23 (1H, dd, J = 7.1, 2.0 Hz), 4.56 (2H, s), 3.75 (3H, s), 2.85 (2H, q, J = 7.6 Hz), 1.33 (3H, t, J = 7.6 Hz).

Reference Production Example 20

[001190] Under cooling, a mixture of 7.00 g of CA14 mentioned in Reference Production Example 14, 9.90 g of calcium carbonate, 80 ml of dioxane, and 80 ml of water was stirred with heating under reflux for 7 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, 4.68 g of 1- (2-hydroxymethyl-3-methylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA20) were obtained.

[001191] 1H-NMR (CDCh) δ (ppm): 7.39-7.34 (2H, m), 7.23-7.18 (1H, m), 4.48 (2H, d, J = 7.1 Hz), 3.75 (3H, s), 2.56 (3H, s).

Reference Production Example 21

[001192] Under cooling, a mixture of 3.00 g of CA19 mentioned in Reference Production Example 19, 4.00 g of calcium carbonate, 50 ml of dioxane, and 50 ml of water was stirred with heating under reflux for 6 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, 2.58 g of 1- (2-hydroxymethyl-3-ethylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA21) were obtained.

[001193] 1H-NMR (CDCl3) δ (ppm): 7.44-7.39 (2H, m), 7.23-7.19 (1H, m), 4.49 (2H, d, J = 7.2 Hz), 3.75 (3H, s), 2.93 (2H, q, J = 7.6 Hz), 1.31 (3H, t, J = 7.6 Hz).

Reference Production Example 22

[001194] Under cooling, a mixture of 3.00 g of CA16 mentioned in Reference Production Example 16, 3.90 g of calcium carbonate, 50 ml of dioxane, and 50 ml of water was stirred with heating under reflux for 6 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, 2.72 g of 1 - (2-hydroxymethyl-3-cyclopropylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA22) were obtained.

[001195] 1H-NMR (CDCI3) δ (ppm): 7.38 (1H, t, J = 7.8 Hz), 7.20 (1H, d, J = 8.0 Hz), 7.16 ( 1H, d, J = 7.7 Hz), 4.68 (2H, d, J = 7.0 Hz), 3.76 (3H, s), 2.39-2.32 (1H, m), 1.10-1.05 (2H, m), 0.79-0.75 (2H, m).

Reference Production Example 23

[001196] Under cooling, 3.00 g of CA7 mentioned in Reference Production Example 7, 4.02 g of calcium carbonate, 50 ml of dioxane, and 50 ml of water were stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, 1.70 g of 1- (2-hydroxymethyl-3-methoxyphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA23) were obtained.

[001197] 1H-NMR (CDCI3) δ (ppm): 7.44 (1H, t, J = 8.2 Hz), 7.07 (1H, d, J = 8.5 Hz), 7.01 ( 1H, d, J = 8.0 Hz), 4.55 (2H, d, J = 7.0 Hz), 3.95 (3H, s), 3.74 (3H, s).

Reference Production Example 24

[001198] Upon cooling, a mixture of 4.87 g of CA3 mentioned in Reference Production Example 3, 6.42 g of calcium carbonate, 50 ml of dioxane, and 50 ml of water was stirred with heating under reflux for 7 hours. After cooling, water was poured into the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, 2.00 g of 1- (2-hydroxymethyl-3-chlorophenyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as CA24) were obtained.

[001199] 1H-NMR (CDCI3) δ (ppm): 7.61 (1H, dd, J = 8.0, 1.1 Hz), 7.43 (1H, t, J = 8.0 Hz), 7.34 (1H, dd, J = 8.0, 1.1 Hz), 4.64 (2H, d, J = 7.3 Hz), 3.76 (3H, s).

Reference Production Example 25

[001200] A 10.0 g mixture of 1- [2- (3-bromophenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one mentioned in Synthesis Example 10, 8 , 12 g of bis (pinacolate) diboro, 7.86 g of potassium acetate, 2.18 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium (ll) dichloromethane addition product, and 200 ml of dimethyl sulfoxide was stirred at 90 ° C for 5 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 9.68 g of 1-methyl-4- {3-methyl-2- [3- (4,4,5,5-tetramethyl- [ 1,3,2] dioxaborolan-2-yl) -phenoxymethyl] -phenyl} -1,4-dihydrotetrazol-5-one (referred to as CA25).

[001201] 1H-NMR (CDCh) δ (ppm): 7.44-7.39 (3H, m), 7.31-7.23 (3H, m), 6.98-6.95 (1H, m), 5.03 (2H, s), 3.63 (3H, s), 2.49 (3H, s), 1.35 (12H, s).

Reference Production Example 26

[001202] A mixture of 8.10 g of (2-amino-6-methylphenyl) methanol produced by the method mentioned in WO 2010/58314 A, 6.94 g of concentrated sulfuric acid, and 450 ml of methanol was stirred at δO 'C for 2 hours. After the reaction mixture was cooled to OX), 5.66 g of sodium hydroxide was added and the mixture was concentrated under reduced pressure. To the residue thus obtained, saturated sodium bicarbonate water was added, followed by extraction with toluene. The organic layer was washed with water and saturated sodium bicarbonate water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 8.62 g of 3-methyl-2-methoxymethyl-1-aminobenzene (referred to as CA26).

[001203] 1H-NMR (CDCl3) δ (ppm): 2.33 (3H, s), 3.36 (3H, s), 4.12 (2H, s), 4.54 (2H, s), 6.55 (1H, d, J = 8.0 Hz), 6.58 (1H, d, J = 7.3 Hz), 7.00 (1H, t, J = 7.7 Hz).

Reference Production Example 27

[001204] A mixture of 6.35 g of CA26 mentioned in Reference Production Example 26, 4.36 g of triphosgene, 150 ml of saturated sodium bicarbonate water, and 150 ml of ethyl acetate was stirred for 1 hour under cooling. The organic layer of the reaction mixture was washed with a saturated saline solution and then concentrated under reduced pressure to obtain 6.30 g of 3-methyl-2-methoxymethyl-1-isocyanatobenzene (referred to as CA27).

[001205] 1H-NMR (CDCl3) δ (ppm): 2.40 (3H, s), 3.42 (3H, s), 4.51 (2H, s), 6.97 (1H, d, J = 8.0 Hz), 7.03 (1H, d, J = 7.6 Hz), 7.16 (1H, t, J = 7.8 Hz).

Reference Production Example 28

[001206] Upon cooling, 6.16 g of anhydrous aluminum chloride was added to 100 ml of N, N-dimethylformamide, followed by stirring for 30 minutes. To this was added 3.00 g of sodium azide, followed by stirring for 30 minutes, the addition of 6.30 g of CA27 mentioned in Reference Production Example 27, and also heating at δO'C for 10 hours. After cooling, the reaction solution was added to a mixture of 4.62 g of sodium nitrite, 100 ml of water, and 100 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with water and a 10% aqueous sodium hydrogen sulfate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 7.00 g of 1- (2-methoxymethyl-3 - methylphenyl) -1,4-dihydrotetrazol-5-one (referred to as CA28).

[001207] 1H-NMR (CDCl3) δ (ppm): 2.49 (3H, s), 3.25 (3H, s), 4.45 (2H, s), 7.24 (1H, t, J = 4.9 Hz), 7.39 (2H, d, J = 4.9 Hz), 13.00 (1H, s).

Reference Production Example 29

[001208] A mixture of 7.20 g of CA28 mentioned in Reference Production Example 28, 13.56 g of potassium carbonate, 3.72 ml of dimethylsulfuric acid, and 150 ml of N, N-dimethylformamide was stirred at room temperature for 1 hour. The water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 6.90 g of CA13 mentioned in Reference Production Example 13. 1H NMR data compared with the values mentioned in Reference Production Example 13.

Reference Production Example 30

[001209] A mixture of 3.0 g of 1- [2- (6-bromopyridin-2-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one mentioned in the Example of Synthesis 1, 4.1 g of bis (pinacolate) diboro, 2.4 g of potassium acetate, 0.65 g of [1,1'-bis (diphenylphosphine) ferrocene] palladium dichloride addition product ll), and 20 ml of dimethyl sulfoxide was stirred at θO'C for 3 hours. After resting to cool, the water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 3.9 g of 1-methyl-4- {3-methyl-2- [6- (4,4,5,5-tetramethyl- [1,3,2] dioxaborolan-2-yl) -pyridin-2-yloxymethyl] -phenyl} -1,4-dihydrotetrazol-5-one (referred to as CA29 ).

[001210] 1H-NMR (CDCh) δ (ppm): 7.91-7.86 (1H, m), 7.62 (1H, d, J = 7.2 Hz), 7.46-7.40 (2H, m), 7.31-7.28 (1H, m), 6.85 (1H, d, J = 8.6 Hz), 5.41 (2H, s), 3.66 (3H, s), 2.56 (3H, s), 1.21 (12H, s).

[001211] According to the processes mentioned above, the following compounds can be obtained:

[001212] compounds Q1A-001 to Q1A-558, Q1B-001 to Q1B-558, Q1C-001 to Q1C-558, Q1D-001 to Q1D-558, Q1E-001 to Q1E-558, Q1F- 001 to Q1F- 558, Q1G-001 to Q1G-558, Q1H-001 to Q1H-558, Q11-001 to Q11-558, QU-001 to QU-558, Q1K-001 to Q1K-558, Q2A-001 to Q2A- 558, Q2B-001 to Q2B-558, Q2C-001 to Q2C-558, Q2D-001 to Q2D-558, Q2E-001 to Q2E-558, Q2F-001 to Q2F-558, Q2G-001 to Q2G-558, Q2H- 001 to Q2H-558, Q2I-001 to Q2I-558, Q2J-001 to Q2J-558, Q2K-001 to Q2K-558, Q3A-001 to Q3A-558, Q3B-001 to Q3B-558, Q3C-001 to Q3C- 558, Q3D-001 to Q3D-558, Q3E-001 to Q3E-558, Q3F-001 to Q3F-558, Q3G-001 to Q3G-558, Q3H-001 to Q3H-558, Q3I-001 to Q3I- 558, Q3J-001 to Q3J-558, Q3K-001 to Q3K-558, Q4A-001 to Q4A-558, Q4B-001 to Q4B-558, Q4C-001 to Q4C-558, Q4D-001 to Q4D-558, Q4E-001 to Q4E-558, Q4F-001 to Q4F-558, Q4G-001 to Q4G-558, Q4H-001 to Q4H-558, Q4I-001 to Q4I-558, Q4J-001 to Q4J-558, Q4K- 001 to Q4K-558, Q5A-001 to Q5A-558, Q5B-001 to Q5B-558, Q5C-001 to Q5C-558, Q5D-001 to Q5D-558, Q5E-001 to Q5E-558, Q5F-001 to Q5F-558, Q5G-001 to Q5G-558, Q5H-001 to Q5H-558, Q5I-001 to Q5I-558, Q5J-001 to Q5J-558, Q5K-001 to Q5K-558, Q6A-001 to Q6A-558, Q6B-001 to Q6B-558, Q6C-001 to Q6C -558, Q6D-001 to Q6D-558, Q6E-001 to Q6E-558, Q6F-001 to Q6F-558, Q6G-001 to Q6G-558, Q6H-001 to Q6H-558, Q6I-001 to Q6I-558 , Q6J-001 to Q6J-558, Q6K-001 to Q6K-558, Q7A-001 to Q7A- 558, Q7B-001 to Q7B-558, Q7C-001 to Q7C-558, Q7D-001 to Q7D-558, Q7E -001 to Q7E-558, Q7F-001 to Q7F-558, Q7G-001 to Q7G-558, Q7H- 001 to Q7H-558, Q7I-001 to Q7I-558, Q7J-001 to Q7J-558, Q7K-001 to Q7K-558, Q8A-001 to Q8A-558, Q8B-001 to Q8B-558, Q8C-001 to Q8C- 558, Q8D-001 to Q8D-558, Q8E-001 to Q8E-558, Q8F-001 to Q8F -558, Q8G-001 to Q8G-558, Q8H-001 to Q8H-558, Q8I-001 to Q8I-558, Q8J-001 to Q8J-558, Q8K-001 to Q8K-558, Q9A-001 to Q9A-558 , Q9B-001 to Q9B-558, Q9C-001 to Q9C-558, Q9D-001 to Q9D-558, Q9E-001 to Q9E-558, Q9F-001 to Q9F-558, Q9G-001 to Q9G-558, Q9H -001 to Q9H-558, Q9I-001 to Q9I-558, Q9J-001 to Q9J-558, Q9K-001 to Q9K-558, Q10A- 001 to Q10A-558, Q10B-001 to Q1 OB-558, Q10C- 001 to Q10C-558, Q10D-001 to Q10D-558, Q1 0E-001 to Q10E-558, Q10F-001 to Q10F- 558, Q10G-001 to Q10G-558, Q10H-001 to Q1 OH-558, Q101-001 to Q10I-558, Q10J-001 to Q10J-558, Q10K -001 to Q1 OK-558, Q11A-001 to Q11A-558, Q11B-001 to Q11B-558, Q11C-001 to Q11C-558, Q11D-001 to Q11D-558, Q11E-001 to Q11E-558, Q11F- 001 to Q11F-558, Q11G-001 to Q11G-558, Q11H-001 to Q11H-558, Q111-001 to Q111-558, Q11J-001 to Q11J-558, Q11K-001 to Q11K-558, Q12A-001 to Q12A- 558, Q12B-001 to Q12B-558, Q12C-001 to Q12C-558, Q12D-001 to Q12D-558, Q12E-001 to Q12E-558, Q12F-001 to Q12F-558, Q12G-001 to Q12G- 558, Q12H-001 to Q12H-558, Q121-001 to Q12I-558, Q12J-001 to Q12J-558, and Q12K-001 to Q12K-558.

[001213] The compounds Q1A-001 to Q12K-558 have the structures shown below:

[001214] where Me represents methyl, Et represents ethyl, and Y represents a substituent corresponding to each of the substituents numbers 1 to 558 shown below.

[001215] For example, Q1A-001 represents a compound represented by the formula (Q1 A) in which Y is a 001 substituent, and is represented by the following formula:

[001216] [substituent number; Y], [001; phenyl group], [002; 2-fluorophenyl group], [003; 3-fluorophenyl group], [004; 4-fluorophenyl group], [005; 2,3-difluorophenyl group], [006; 2,4-difluorophenyl group], [007; 2,5-difluorophenyl group], [008; 2,6-difluorophenyl group], [009; 3,4-difluorophenyl group], [010; 3,5-difluorophenyl group], [011; 2,3,4-trifluorophenyl group], [012; 2,3,5-trifluorophenyl group], [013; 2,3,6-trifluorophenyl group], [014; 2,4,5-trifluorophenyl group], [015; 2,4,6-trifluorophenyl group], [016; 3,4,5-trifluorophenyl group], [017; 2,3,4,6-tetrafluorophenyl group], [018; 2,3,5,6-tetrafluorophenyl group], [019; 2,3,4,5,6-pentafluorophenyl group], [020; 2-chlorophenyl group], [021; 3-chlorophenyl group], [022; 4-chlorophenyl group], [023; 2,3-dichlorophenyl group], [024; 2,4-dichlorophenyl group], [025; 2,5-dichlorophenyl group], [026; 2,6-dichlorophenyl group], [027; 3,4-dichlorophenyl group], [028; 3,5-dichlorophenyl group], [029; 2,3,4-trichlorophenyl group]

[001217] [substituent number; Y], [030; 2,3,5-trichlorophenyl group], [031; 2,3,6-trichlorophenyl group], [032; 2,4,5-trichlorophenyl group], [033; 2,4,6-trichlorophenyl group], [034; 3,4,5-trichlorophenyl group], [035; 2,3,4,6-tetrachlorophenyl group], [036; 2,3,5,6-tetrachlorophenyl group], [037; 2,3,4,5,6-pentachlorophenyl] group, [038; 2-bromophenyl group], [039; 3-bromophenyl group], [040; 4-bromophenyl group], [041; 2,4-dibromophenyl group], [042; 2,5-dibromophenyl group], [043; 2,6-dibromophenyl group], [044; 2,4,6-tribromophenyl group], [045; group 2,3,4,5,6-pentabromophenyl], [046; 2-iodophenyl group], [047; 3-iodophenyl group], [048; 4-iodophenyl group], [049; 2,4-diiodophenyl group], [050; 2-chloro-3-fluorophenyl group], [051; 2-chloro-4-fluorophenyl group], [052; 2-chloro-5-fluorophenyl group], [053; 2-chloro-6-fluorophenyl group], [054; 2-chloro-3-bromophenyl group], [055; 2-chloro-4-bromophenyl group], [056; 2-chloro-5-bromophenyl group], [057; 2-chloro-6-bromophenyl group], [058; group 2- bromo-3-chlorophenyl]

[001218] [substituent number; Y], [059; 2-bromo-4-chlorophenyl group], [060; 2-bromo-5-chlorophenyl group], [061; 2-bromo-3-fluorophenyl group], [062; 2-bromo-4-fluorophenyl group], [063; 2-bromo-5-fluorophenyl group], [064; 2-bromo-6-fluorophenyl group], [065; 2-fluoro-3-chlorophenyl group], [066; 2-fluoro-4-chlorophenyl group], [067; 2-fluoro-5-chlorophenyl group], [068; 2-fluoro-4-bromophenyl group], [069; 3-chloro-4-fluorophenyl group], [070; 3-chloro-5-fluorophenyl group], [071; 3-chloro-4-bromophenyl group], [072; 3-chloro-5-bromophenyl group], [073; 3-fluoro-4-chlorophenyl group], [074; 3-fluoro-4-bromophenyl group], [075; 3-bromo-4-chlorophenyl group], [076; 3-bromo-4-fluorophenyl group], [077; 2,6-dichloro-4-bromophenyl group], [078; 2,3-difluoro-4-chlorophenyl group], [079; 2,6-difluoro-4-chlorophenyl group], [080; 2,5-difluoro-4-chlorophenyl group], [081; 3,5-difluoro-4-chlorophenyl group], [082; 2,3,5-trifluoro-4-chlorophenyl] group, [083; 2,3,6-trifluoro-4-chlorophenyl group], [084; 2,3,5,6-tetrafluoro-4-chlorophenyl group], [085; 2,3-difluoro-4-bromophenyl group], [086; 2,6-difluoro-4-bromophenyl group], [087; group 2,5- difluoro-4-bromophenyl]

[001219] [substituent number; Y], [088; 3,5-difluoro-4-bromophenyl group], [089; 2,3,5-trifluoro-4-bromophenyl group], [090; 2,3,6-trifluoro-4-bromophenyl group], [091; 2,3,5,6-tetrafluoro-4-bromophenyl group], [092; 2-fluoro-4-iodophenyl group], [093; 3-fluoro-4-iodophenyl group], [094; 2,3-difluoro-4-iodophenyl group], [095; 2,6-difluoro-4-iodophenyl group], [096; 2,5-difluoro-4-iodophenyl group], [097; 3,5-difluoro-4-iodophenyl group], [098; 2,3,5-trifluoro-4-iodophenyl group], [099; 2,3,6-trifluoro-4-iodophenyl group], [100; 2,3,5,6-tetrafluoro-4-iodophenyl group], [101; 2-methylphenyl group], [102; 3-methylphenyl group], [103; 4-methylphenyl group], [104; 2,3-dimethylphenyl group], [105; 2,4-dimethylphenyl group], [106; 2,5-dimethylphenyl group], [107; 2,6-dimethylphenyl group], [108; 3,4-dimethylphenyl group], [109; 3,5-dimethylphenyl group], [110; 2,3,5-trimethylphenyl group], [111; 2,3,4-trimethylphenyl group], [112; 2,3,6-trimethylphenyl group], [113; 2,4,5-trimethylphenyl group], [114; 2,4,6-trimethylphenyl group], [115; 3,4,5-trimethylphenyl group], [116; 2,3,4,6-tetramethylphenyl group]

[001220] [substituent number; Y], [117; 2,3,5,6-tetramethylphenyl group], [118; 2,3,4,5,6-pentamethylphenyl group], [119; 2-ethylphenyl group], [120; 3-ethylphenyl group], [121; 4-ethylphenyl group], [122; 2,4-diethylphenyl group], [123; 2,6-diethylphenyl group], [124; 3,5-diethylphenyl group], [125; 2,4,6-triethylphenyl group], [126; 2-n-propylphenyl group], [127; 3-n-propylphenyl group], [128; 4-n-propylphenyl group], [129; 2-isopropylphenyl group], [130; 3-isopropylphenyl group], [131; 4- isopropylphenyl group], [132; 2,4-diisopropylphenyl group], [133; 2,6-diisopropylphenyl group], [134; 3,5-diisopropylphenyl group], [135; 2-s-butylphenyl group], [136; 3-s-butylphenyl group], [137; 4-s-butylphenyl group], [138; 2-t-butylphenyl group], [139; 3-t-butylphenyl group], [140; 4-t-butylphenyl group], [141; 4-n-butylphenyl group], [142; 4-n-nonylphenyl group], [143; 2-methyl-4-t-butylphenyl group], [144; 2-methyl-6-t-butylphenyl group], [145; 2-methyl-4-isopropylphenyl group]

[001221] [substituent number; Y], [146; 2-methyl-5-isopropylphenyl group], [147; 3-methyl-4-isopropylphenyl group], [148; 2-cyclopropylphenyl group], [149; 3-cyclopropylphenyl group], [150; 4-cyclopropylphenyl group], [151; 4-cyclobutylphenyl group], [152; 4-cyclopentylphenyl group], [153; 4-hydroxylphenyl group], [154; 2-methoxyphenyl group], [155; 3-methoxyphenyl group], [156; 4-methoxyphenyl group], [157; 2-ethoxyphenyl group], [158; 3-ethoxyphenyl group], [159; 4- ethoxyphenyl group], [160; 2-n-propyloxyphenyl group], [161; 3-n-propyloxyphenyl group], [162; 4-n-propyloxyphenyl group], [163; 2-isopropyloxyphenyl group], [164; 3-isopropyloxyphenyl group], [165; 4- isopropyloxyphenyl group], [166; 2-n-hexyloxyphenyl group], [167; 3-n-hexyloxyphenyl group], [168; 4-n-hexyloxyphenyl group], [169; 2-benzyloxyphenyl group], [170; 3-benzyloxyphenyl group], [171; 4-benzyloxyphenyl group], [172; 2,3-dimethoxyphenyl group], [173; 2,4-dimethoxyphenyl group], [174; 2,5-dimethoxyphenyl group]

[001222] [substituent number; Y], [175; 2,6-dimethoxyphenyl group], [176; 3,4-dimethoxyphenyl group], [177; 3,5-dimethoxyphenyl group], [178; 2-t-butoxyphenyl group], [179; 3-t-butoxyphenyl group], [180; 4-t-butoxyphenyl group], [181; 2-trifluoromethoxyphenyl group], [182; 3-trifluoromethoxyphenyl group], [183; 4-trifluoromethoxyphenyl group], [184; 2- pentafluoroethoxyphenyl group], [185; 3-pentafluoroethoxyphenyl group], [186; 4-pentafluoroethoxyphenyl group], [187; 2-phenoxyphenyl group], [188; 3-phenoxyphenyl group], [189; 4-phenoxyphenyl group], [190; 4- (2'-fluorophenoxy) phenyl] group, [191; 4- (3'-chlorophenoxy) phenyl] group, [192; 4- (4'-chlorophenoxy) phenyl] group, [193; 2,3,6-trimethyl-4-fluorophenyl group], [194; 2,3,6-trimethyl-4-chlorophenyl group], [195; 2,3,6-trimethyl-4-bromophenyl group], [196; 2,4-dimethyl-6-fluorophenyl group], [197; 2,4-dimethyl-6-chlorophenyl group], [198; 2,4-dimethyl-6-bromophenyl group], [199; 2-isopropyl-4-chloro-5-methylphenyl group], [200; 2-methyl-5-isopropyl-4-chlorophenyl group], [201; 3-fluoro-2-methoxyphenyl group], [202; 4-fluoro-2-methoxyphenyl group], [203; 5-fluoro-2-methoxyphenyl group]

[001223] [substituent number; Y], [204; 6-fluoro-2-methoxyphenyl group], [205; 2-fluoro-3-methoxyphenyl group], [206; 4-fluoro-3-methoxyphenyl group], [207; 5-fluoro-3-methoxyphenyl group], [208; 6-fluoro-3-methoxyphenyl group], [209; 2-fluoro-4-methoxyphenyl group], [210; 3-fluoro-4-methoxyphenyl group], [211; 3,4-difluoro-2-methoxyphenyl group], [212; 3,5-difluoro-2-methoxyphenyl group], [213; 3,6-difluoro-2-methoxyphenyl group], [214; 4,5-difluoro-2-methoxyphenyl], [215; 4,6-difluoro-2-methoxyphenyl], [216; 5,6-difluoro-2-methoxyphenyl], [217; 2,4-difluoro-3-methoxyphenyl group], [218; 2,5-difluoro-3-methoxyphenyl group], [219; 2,6-difluoro-3-methoxyphenyl group], [220; 4,5-difluoro-3-methoxyphenyl], [221; 4,6-difluoro-3-methoxyphenyl], [222; 5,6-difluoro-3-methoxyphenyl], [223; 2,3-difluoro-4-methoxyphenyl group], [224; 2,5-difluoro-4-methoxyphenyl group], [225; 2,6-difluoro-4-methoxyphenyl group], [226; 3,5-difluoro-4-methoxyphenyl group], [227; 3,6-difluoro-4-methoxyphenyl group], [228; 2,3,5-trifluoro-4-methoxyphenyl group], [229; 2,3,5,6-tetrafluoro-4-methoxyphenyl group], [230; 3-chloro-2-methoxyphenyl group], [231; 4-chloro-2-methoxyphenyl group], [232; 5-chloro-2-methoxyphenyl group]

[001224] [substituent number; Y], [233; 6-chloro-2-methoxyphenyl group], [234; 2-chloro-3-methoxyphenyl group], [235; 4-chloro-3-methoxyphenyl group], [236; 5-chloro-3-methoxyphenyl group], [237; 6-chloro-3-methoxyphenyl group], [238; 2-chloro-4-methoxyphenyl group], [239; 3-chloro-4-methoxyphenyl group], [240; 3,4-dichloro-2-methoxyphenyl group], [241; 3,5-dichloro-2-methoxyphenyl group], [242; 3,6-dichloro-2-methoxyphenyl group], [243; 4,5-dichloro-2-methoxyphenyl], [244; 4,6-dichloro-2-methoxyphenyl], [245; 5,6-dichloro-2-methoxyphenyl], [246; 2,4-dichloro-3-methoxyphenyl group], [247; 2,5-dichloro-3-methoxyphenyl group], [248; 2,6-dichloro-3-methoxyphenyl group], [249; 4,5-dichloro-3-methoxyphenyl], [250; 4,6-dichloro-3-methoxyphenyl], [251; 5,6-dichloro-3-methoxyphenyl], [252; 2,3-dichloro-4-methoxyphenyl group], [253; 2,5-dichloro-4-methoxyphenyl group], [254; 2,6-dichloro-4-methoxyphenyl group], [255; 3,5-dichloro-4-methoxyphenyl group], [256; 3,6-dichloro-4-methoxyphenyl group], [257; 3-fluoro-2-trifluoromethoxyphenyl group], [258; 4-fluoro-2-trifluoromethoxyphenyl group], [259; 5-fluoro-2-trifluoromethoxyphenyl group], [260; 6-fluoro-2-trifluoromethoxyphenyl group], [261; 2-fluoro-3-trifluoromethoxyphenyl group]

[001225] [substituent number; Y], [262; 4-fluoro-3-trifluoromethoxyphenyl group], [263; 5-fluoro-3-trifluoromethoxyphenyl group], [264; 6-fluoro-3-trifluoromethoxyphenyl group], [265; 2-fluoro-4-trifluoromethoxyphenyl group], [266; 3-fluoro-4-trifluoromethoxyphenyl group], [267; 3,4-difluoro-2-trifluoromethoxyphenyl group], [268; 3,5-difluoro-2-trifluoromethoxyphenyl group], [269; 3,6-difluoro-2-trifluoromethoxyphenyl group], [270; 4,5-difluoro-2-trifluoromethoxyphenyl], [271; 4,6-difluoro-2-trifluoromethoxyphenyl], [272; 5,6-difluoro-2-trifluoromethoxyphenyl], [273; 2,4-difluoro-3-trifluoromethoxyphenyl group], [274; 2,5-difluoro-3-trifluoromethoxyphenyl group], [275; 2,6-difluoro-3-trifluoromethoxyphenyl group], [276; 4,5-difluoro-3-trifluoromethoxyphenyl], [277; 4,6-difluoro-3-trifluoromethoxyphenyl], [278; 5,6-difluoro-3-trifluoromethoxyphenyl], [279; 2,3-difluoro-4-trifluoromethoxyphenyl group], [280; 2,5-difluoro-4-trifluoromethoxyphenyl group], [281; 2,6-difluoro-4-trifluoromethoxyphenyl group], [282; 3,5-difluoro-4-trifluoromethoxyphenyl group], [283; 3,6-difluoro-4-trifluoromethoxyphenyl group], [284; 2,3,5-trifluoro-4-trifluoromethoxyphenyl group], [285; 2,3,5,6-tetrafluoro-4-trifluoromethoxyphenyl group], [286; 3-chloro-2-trifluoromethoxyphenyl group], [287; 4-chloro-2-trifluoromethoxyphenyl group], [288; 5-chloro-2-trifluoromethoxyphenyl group], [289; 6-chloro-2-trifluoromethoxyphenyl group], [290; 2-chloro-3-trifluoromethoxyphenyl group]

[001226] [substituent number; Y], [291; 4-chloro-3-trifluoromethoxyphenyl group], [292; 5-chloro-3-trifluoromethoxyphenyl group], [293; 6-chloro-3-trifluoromethoxyphenyl group], [294; 2-chloro-4-trifluoromethoxyphenyl group], [295; 3-chloro-4-trifluoromethoxyphenyl group], [296; 3,4-dichloro-2-trifluoromethoxyphenyl group], [297; 3,5-dichloro-2-trifluoromethoxyphenyl group], [298; 3,6-dichloro-2-trifluoromethoxyphenyl group], [299; 4,5-dichloro-2-trifluoromethoxyphenyl], [300; 4,6-dichloro-2-trifluoromethoxyphenyl], [301; 5,6-dichloro-2-trifluoromethoxyphenyl], [302; 2,4-dichloro-3-trifluoromethoxyphenyl group], [303; 2,5-dichloro-3-trifluoromethoxyphenyl group], [304; 2,6-dichloro-3-trifluoromethoxyphenyl group], [305; 4,5-dichloro-3-trifluoromethoxyphenyl], [306; 4,6-dichloro-3-trifluoromethoxyphenyl], [307; 5,6-dichloro-3-trifluoromethoxyphenyl], [308; 2,3-dichloro-4-trifluoromethoxyphenyl group], [309; 2,5-dichloro-4-trifluoromethoxyphenyl group], [310; 2,6-dichloro-4-trifluoromethoxyphenyl group], [311; 3,5-dichloro-4-trifluoromethoxyphenyl group], [312; 3,6-dichloro-4-trifluoromethoxyphenyl group], [313; 2-carbamoylphenyl group], [314; 3-carbamoylphenyl group], [315; 4-carbamoylphenyl group], [316; group 2- (N-methylaminocarbonyl) phenyl], [317; group 3- (N-methylaminocarbonyl) phenyl], [318; group 4- (N-methylaminocarbonyl) phenyl], [319; 2- (N, N-dimethylaminocarbonyl) phenyl group]

[001227] [substituent number; Y], [320; group 3- (N, N-dimethylaminocarbonyl) phenyl], [321; group 4- (N, N-dimethylaminocarbonyl) phenyl], [322; 2-methoxycarbonylphenyl group], [323; 3-methoxycarbonylphenyl group], [324; 4-methoxycarbonylphenyl group], [325; 4-acetoxyphenyl group], [326; 2-methoxymethylphenyl group], [327; 3-methoxymethylphenyl group], [3], [8; 4-methoxymethylphenyl group], [329; 2-formylphenyl group], [330; 3-formylphenyl group], [331; 4-formylphenyl group], [332; 2-methyl-5-bromophenyl group], [333; 2-methyl-6-bromophenyl group], [334; 2-chloro-3-methylphenyl group], [335; 2-chloro-4-methylphenyl group], [336; 2-chloro-5-methylphenyl group], [337; 2-fluoro-3-methylphenyl group], [338; 2-fluoro-4-methylphenyl group], [339; 2-fluoro-5-methylphenyl group], [340; 2-bromo-3-methylphenyl group], [341; 2-bromo-4-methylphenyl group], [342; 2-bromo-5-methylphenyl group], [343; 3-methyl-4-chlorophenyl group], [344; 3-methyl-5-chlorophenyl group], [345; 3-methyl-4-fluorophenyl group], [346; 3-methyl-5-fluorophenyl group], [347; 3-methyl-4-bromophenyl group], [348; 3-methyl-5-bromophenyl group]

[001228] [substituent number; Y], [349; 3-fluoro-4-methylphenyl group], [350; 3-chloro-4-methylphenyl group], [351; 3-bromo-4-methylphenyl group], [352; 2-chloro-4,5-dimethylphenyl group], [353; 2-bromo-4,5-dimethylphenyl group], [354; 2-chloro-3,5-dimethylphenyl group], [355; 2-bromo-3,5-dimethylphenyl group], [356; 2,6-dibromo-4-methylphenyl group], [357; 2,4-dichloro-6-methylphenyl group], [358; 2,4-difluoro-6-methylphenyl group], [359; 2,4-dibromo-6-methylphenyl group], [360; 2,6-dimethyl-4-fluorophenyl group], [361; 2,6-dimethyl-4-chlorophenyl group], [362; 2,6-dimethyl-4-bromophenyl group], [363; 3,5-dimethyl-4-fluorophenyl group], [364; 3,5-dimethyl-4-chlorophenyl group], [365; 3,5-dimethyl-4-bromophenyl group], [366; 2,3-difluoro-4-methylphenyl group], [367; 2,5-difluoro-4-methylphenyl group], [368; 3,5-difluoro-4-methylphenyl group], [369; 2,3,5-trifluoro-4-methylphenyl group], [370; 2,3,6-trifluoro-4-methylphenyl group], [371; 2,3,5,6-tetrafluoro-4-methylphenyl group], [372; 2-fluoro-4-ethylphenyl group], [373; 3-fluoro-4-ethylphenyl group], [374; 2,3-difluoro-4-ethylphenyl group], [375; 2,6-difluoro-4-ethylphenyl group], [376; 2,5-difluoro-4-ethylphenyl group], [377; 3,5-difluoro-4-ethylphenyl group]

[001229] [substituent number; Y], [378; 2,3,5-trifluoro-4-ethylphenyl group], [379; 2,3,6-trifluoro-4-ethylphenyl group], [380; 2,3,5,6-tetrafluoro-4-ethylphenyl group], [381; 2-trifluoromethylphenyl group], [382; 3-trifluoromethylphenyl group], [383; 4-trifluoromethylphenyl group], [384; group 4- (2,2,2-trifluoro-1-trifluoromethyl-ethyl) phenyl], [385; group 4- (2,2-difluoroethoxy) phenyl], [386; group 4- (2,2,2-trifluoroethoxy) phenyl], [387; 2-nitrophenyl group], [388; 3-nitrophenyl group], [389; 4-nitrophenyl group], [390; 2-cyanophenyl group], [391; 3-cyanophenyl group], [392; group 4- cyanophenyl], [393; 2-methyl-3-chlorophenyl group], [394; 2-methyl-4-chlorophenyl group], [395; 2-methyl-5-chlorophenyl group], [396; 2-methyl-6-chlorophenyl group], [397; 2-methyl-3-fluorophenyl group], [398; 2-methyl-4-fluorophenyl group], [399; 2-methyl-5-fluorophenyl group], [400; 2-methyl-6-fluorophenyl group], [401; 2-methyl-3-bromophenyl group], [402; 2-methyl-4-bromophenyl group], [403; 4-methylthiophenyl group], [404; 4-methylsulfonylphenyl group], [405; 4-methylsulfinylphenyl group], [406; 4- trifluoromethylthiophenyl group]

[001230] [substituent number; Y], [407; 4-ethynylphenyl group], [408; 4- (1-propynyl) phenyl] group, [409; 4-vinylphenyl group], [410; group 4- (2,2-dichlorovinyl) phenyl], [411; group 4- (2,2-difluorovinyl) phenyl], [412; cyclohexyl], [413; 2-chlorocyclohexyl group], [414; 3-chlorocyclohexyl group], [415; 4-chlorocyclohexyl group], [416; 4,4-dichlorocyclohexyl], [417; 2-bromocyclohexyl group], [418; 3-bromocyclohexyl group], [419; 4-bromocyclohexyl group], [420; 4,4-dibromocyclohexyl], [421; 2-iodocyclohexyl group], [422; 3-iodocyclohexyl group], [423; 4- iodocyclohexyl group], [424; 2-fluorocyclohexyl group], [425; 3-fluorocyclohexyl group], [426; 4-fluorocyclohexyl group], [427; 4,4- difluorocyclohexyl], [428; 4-methylcyclohexyl group], [429; 4- ethylcyclohexyl group], [430; 4-methoxycyclohexyl group], [431; 4- ethoxycyclohexyl group], [432; 4-trifluoromethoxycyclohexyl group], [433; 1-cyclohexenyl], [434; 2-cyclohexenyl group], [435; 3-cyclohexenyl group]

[001231] [substituent number; Y], [436; 4-fluoro-1-cyclohexenyl group], [437; 4-fluoro-2-cyclohexenyl group], [438; group 4-fluoro-3-cyclohexenyl],

[001232] [439; 2-chloro-1-cyclohexenyl group], [440; 3-chloro-1-cyclohexenyl group], [441; 4-chloro-1-cyclohexenyl group], [442; group 5-chloro-1-cyclohexenyl], [443; 6-chloro-1-cyclohexenyl group], [444; 1-chloro-2-cyclohexenyl], [445; 2-chloro-2-cyclohexenyl group], [446; 3-chloro-2-cyclohexenyl group], [447; 4-chloro-2-cyclohexenyl group], [448; 5-chloro-2-cyclohexenyl group], [449; 6-chloro-2-cyclohexenyl group], [450; 1-chloro-3-cyclohexenyl], [451; 2-chloro-3-cyclohexenyl group], [452; 3-chloro-3-cyclohexenyl group], [453; 4-chloro-3-cyclohexenyl group], [454; 5-chloro-3-cyclohexenyl group], [455; 6-chloro-3-cyclohexenyl group], [456; 4-bromo-1-cyclohexenyl group], [457; 4-bromo-2-cyclohexenyl group], [458; 4-bromo-3-cyclohexenyl group], [459; 4-methyl-1-cyclohexenyl group], [460; 4-methyl-2-cyclohexenyl group], [461; 4-methyl-3-cyclohexenyl group], [462; 4-ethyl-1-cyclohexenyl group], [463; 4-ethyl-2-cyclohexenyl group], [464; 4-ethyl-3-cyclohexenyl group]

[001233] [substituent number; Y], [465; 4-methoxy-1-cyclohexenyl group], [466; 4-methoxy-2-cyclohexenyl group], [467; 4-trifluoromethoxy-1-cyclohexenyl group], [468; 4-trifluoromethoxy-2-cyclohexenyl group], [469; morpholino], [470; thiomorpholino], [471; piperidino], [472; 4-methoxypiperidine group], [473; piperazinyl], [474; N-methylpiperazinyl], [475; pyrrolyl], [476; imidazolyl], [477; pyrazolyl], [478; 4-methyl-pyrazol-1-yl group], [479; 4,5-dimethyl-pyrazol-1-yl], [480; 3-methyl-pyrazol-1-yl group], [481; 3,4-dimethyl-pyrazol-1-yl group], [482; 4-methoxy-3,5-dimethyl-pyrazol-1-yl group], [483; 1-methyl-1 H-pyrazol-3-yl], [484; 1,4,5-trimethyl-1 H-pyrazol-3-yl], [485; 1,4-dimethyl-5-methoxy-1H-pyrazol-3-yl], [486; 2-pyridyl group], [487; 3-pyridyl group], [488; 4-pyridyl group], [489; 5-methoxy-2-pyridyl group], [490; 5-trifluoromethoxy-2-pyridyl group], [491; 5-fluoro-2-pyridyl group], [492; 5-chloro-2-pyridyl group], [493; 6-methoxy-3-pyridyl group]

[001234] [substituent number; Y], [494; 6-trifluoromethoxy-3-pyridyl group], [495; 6-fluoro-3-pyridyl group], [496; 6-chloro-3-pyridyl group], [497; 5-methoxy-2-pyrazinyl group], [498; 5-trifluoromethoxy-2-pyrazinyl group], [499; 5-fluoro-2-pyrazinyl group], [500; 5-chloro-2-pyrazinyl group], [501; 5-methoxy-2-pyrimidinyl group], [502; 5-trifluoromethoxy-2-pyrimidinyl group], [503; 5-fluoro-2-pyrimidinyl group], [504; 5-chloro-2-pyrimidinyl group], [505; 6-methoxy-3-pyridazinyl group], [506; 6-trifluoromethoxy-3-pyridazinyl group], [507; 6-fluoro-3-pyridazinyl group], [508; 6-chloro-3-pyridazinyl group], [509; 1-naphthyl], [510; 2-naphthyl group], [511; 2-quinolyl group], [512; 3-quinolyl group], [513; 4-quinolyl group], [514; 5-quinolyl group], [515; 6-quinolyl group], [516; 7-quinolyl], [517; 8-quinolyl], [518; 3-isoquinolyl group], [519; 6- isoquinolyl group], [520; 7-isoquinolyl], [521; 3,4-methylenedioxyphenyl group]

[001235] [substituent number; Y], [522; 2-ethoxy-4-methoxyphenyl group], [523; 2-isopropyloxy-4-methoxyphenyl group], [524; 4-ethoxy-2-methoxyphenyl group], [525; 4-isopropyloxy-2-methoxyphenyl group], [526; 4-fluoro-2-isopropyloxyphenyl group], [527; 4-chloro-2-isopropyloxyphenyl group], [528; 4-bromo-2-isopropyloxyphenyl group], [529; 4-fluoro-2-ethoxyphenyl group], [530; 4-chloro-2-ethoxyphenyl group], [531; 4-bromo-2-ethoxyphenyl group], [532; 4-cyano-2-methoxyphenyl group], [533; 4-cyano-2-ethoxyphenyl group], [534; 4-cyano-2-isopropyloxyphenyl group], [535; 2-methoxy-3-pyridyl group], [536; 6-chloro-2-methoxy-3-pyridyl group], [537; 6-fluoro-2-methoxy-3-pyridyl group], [538; 6-bromo-2-methoxy-3-pyridyl group], [539; 6-ethoxy-2-methoxy-3-pyridyl group], [540; 2,6-dimethoxy-3-pyridyl group], [541; 6-trifluoromethyl-2-methoxy-3-pyridyl group], [542; group 6- cyano-2-methoxy-3-pyridyl]

[001236] [543; 2-ethoxy-3-pyridyl group], [544; 6-chloro-2-ethoxy-3-pyridyl group], [545; 6-fluoro-2-ethoxy-3-pyridyl group], [546; 6-bromo-2-ethoxy-3-pyridyl group], [547; 2-ethoxy-6-methoxy-3-pyridyl group], [548; 2,6-diethoxy-3-pyridyl group], [549; 6-trifluoromethyl-2-ethoxy-3-pyridyl group], [550; 6-cyano-2-ethoxy-3-pyridyl group], [551; 2-isopropyloxy-3-pyridyl group], [552; 6-chloro-2-isopropyloxy-3-pyridyl group], [553; 6-fluoro-2-isopropyloxy-3-pyridyl group], [554; 6-bromo-2-isopropyloxy-3-pyridyl group], [555; 2-isopropyloxy-6-methoxy-3-pyridyl group], [556; 2,6-diisopropyloxy-3-pyridyl group], [557; 6-trifluoromethyl-2-isopropyloxy-3-pyridyl group], [558; 6-cyano-2-isopropyloxy-3-pyridyl group]

[001237] According to the above process, it is possible to obtain the compounds TH F-Q1-001 to THCFF-Q12-558.

[001238] THF-Q1-001 to THCFF-Q12-558 compounds are compounds represented by the following formulas:

[001239] where X1, X2, X3, and X4 represents any of the combinations Q1 to Q12 shown in Table 42, and Y represents a subsituent corresponding to each of the substituents numbers 1 to 558. [Table 42]

[001240] A tetrazolinone compound in which X1, X2, X, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THF) (referred to as the THF compound).

[001241] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and substituent Y is any of the number 1 to 558 substituents in the THF compound.

[001242] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THF compound.

[001243] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THF compound.

[001244] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THF compound.

[001245] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THF compound.

[001246] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THF compound.

[001247] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and substituent Y is any of the number substituents 1 to 558 in the THF compound.

[001248] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THF compound.

[001249] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THF compound.

[001250] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THF compound.

[001251] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and substituent Y is any of the number 1 to 558 substituents in the THF compound.

[001252] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THC) (referred to as the THC compound).

[001253] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THC compound.

[001254] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THC compound.

[001255] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THC compound.

[001256] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THC compound.

[001257] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THC compound.

[001258] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and substituent Y is any of the number 1 to 558 substituents in the THC compound.

[001259] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THC compound.

[001260] A tetrazolinone compound in which X1, X2, X3, and X4 are shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THC compound.

[001261] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THC compound.

[001262] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THC compound.

[001263] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THC compound.

[001264] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THB) (referred to as the THB compound).

[001265] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THB compound.

[001266] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THB compound.

[001267] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the Y substituent is any of the 1 to 558 substituents in the THB compound.

[001268] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THB compound.

[001269] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THB compound.

[001270] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THB compound.

[001271] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THB compound.

[001272] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THB compound.

[001273] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and the Y substituent is any of the 1 to 558 substituents in the THB compound.

[001274] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THB compound.

[001275] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THB compound.

[001276] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THI) (referred to as the THI compound).

[001277] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THI compound.

[001278] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THI compound.

[001279] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THI compound.

[001280] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THI compound.

[001281] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THI compound.

[001282] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and the Y substituent is any of the 1 to 558 substituents in the THI compound.

[001283] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THI compound.

[001284] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the compound THI.

[001285] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THI compound.

[001286] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THI compound.

[001287] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THI compound.

[001288] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THM) (referred to as the THM compound).

[001289] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THM compound.

[001290] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THM compound.

[001291] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the Y substituent is any of the substituents number 1 to 558 in the THM compound.

[001292] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THM compound.

[001293] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the Y substituent is any of the 1 to 558 substituents in the THM compound.

[001294] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THM compound.

[001295] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THM compound.

[001296] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THM compound.

[001297] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THM compound.

[001298] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THM compound.

[001299] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THM compound.

[001300] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THE) (referred to as the compound THE).

[001301] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THE compound.

[001302] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in compound THE.

[001303] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in compound THE.

[001304] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in compound THE

[001305] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in compound THE.

[001306] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in compound THE.

[001307] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in compound THE.

[001308] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THE compound.

[001309] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in compound THE.

[001310] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THE compound.

[001311] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in compound THE.

[001312] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THMT) (referred to as the THMT compound).

[001313] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THMT compound.

[001314] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THMT compound.

[001315] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THMT compound.

[001316] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the compound THMT.

[001317] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the compound THMT.

[001318] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THMT compound.

[001319] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THMT compound.

[001320] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THMT compound.

[001321] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THMT compound.

[001322] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THMT compound.

[001323] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the compound THMT.

[001324] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THCY) (referred to as the THCY compound).

[001325] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THCY compound.

[001326] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the compound THCY.

[001327] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the compound THCY.

[001328] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCY compound.

[001329] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCY compound.

[001330] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCY compound.

[001331] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the compound THCY.

[001332] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCY compound.

[001333] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THCY compound.

[001334] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THCY compound.

[001335] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THCY compound.

[001336] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and the Y substituent is any of the substituents number 1 to 558 in a compound represented by the formula (THMO) (referred to as the THMO compound).

[001337] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and substituent Y is any of the number 1 to 558 substituents in the THMO compound.

[001338] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the compound THMO.

[001339] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THMO compound.

[001340] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THMO compound.

[001341] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THMO compound.

[001342] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THMO compound.

[001343] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THMO compound.

[001344] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THMO compound.

[001345] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THMO compound.

[001346] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and substituent Y is any of the number substituents 1 to 558 in the THMO compound.

[001347] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THMO compound.

[001348] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THET) (referred to as the THET compound).

[001349] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THET compound.

[001350] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THET compound.

[001351] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the Y substituent is any of the 1 to 558 substituents in the THET compound.

[001352] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THET compound.

[001353] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the Y substituent is any of the 1 to 558 substituents in the THET compound.

[001354] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THET compound.

[001355] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THET compound.

[001356] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THET compound.

[001357] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and the Y substituent is any of the 1 to 558 substituents in the THET compound.

[001358] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THET compound.

[001359] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THET compound.

[001360] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THCF) (referred to as the THCF compound).

[001361] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THCF compound.

[001362] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THCF compound.

[001363] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THCF compound.

[001364] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and the substituent Y is any of the number substituents 1 to 558 in the THCF compound.

[001365] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THCF compound.

[001366] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THCF compound.

[001367] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and the Y substituent is any of the number substituents 1 to 558 in the THCF compound.

[001368] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THCF compound.

[001369] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and substituent Y is any one of the substituents number 1 to 558 in the THCF compound.

[001370] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THCF compound.

[001371] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THCF compound.

[001372] A tetrazolinone compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (THCFF) (referred to as the THCFF compound).

[001373] A tetrazolinone compound in which X1, X2, X3, and X4 are Q2 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001374] A tetrazolinone compound in which X1, X2, X3, and X4 are Q3 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001375] A tetrazolinone compound in which X1, X2, X3, and X4 are Q4 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001376] A tetrazolinone compound in which X1, X2, X3, and X4 are Q5 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001377] A tetrazolinone compound in which X1, X2, X3, and X4 are Q6 shown in Table 42, and the Y substituent is any of the substituents number 1 to 558 in the THCFF compound.

[001378] A tetrazolinone compound in which X1, X2, X3, and X4 are Q7 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001379] A tetrazolinone compound in which X1, X2, X3, and X4 are Q8 shown in Table 42, and the Y substituent is any of the substituents number 1 to 558 in the THCFF compound.

[001380] A tetrazolinone compound in which X1, X2, X3, and X4 are Q9 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001381] A tetrazolinone compound in which X1, X2, X3, and X4 are Q10 shown in Table 42, and substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001382] A tetrazolinone compound in which X1, X2, X3, and X4 are Q11 shown in Table 42, and the Y substituent is any of the number 1 to 558 substituents in the THCFF compound.

[001383] A tetrazolinone compound in which X1, X2, X3, and X4 are Q12 shown in Table 42, and the substituent Y is any of the substituents number 1 to 558 in the THCFF compound.

[001384] For example, a compound in which X1, X2, X3, and X4 are Q1 shown in Table 42, and Y is a number 1 substituent in formula (THF) represents the following compound.

[001385] According to the method mentioned above, it is possible to obtain intermediates TZF-T01 to TZCFF-T12.

[001386] Intermediates TZF-T01 to TZCFF-T12 are compounds represented by the following formulas:

[001387] where X1, X2, and Zx represent any of the combinations T1 to T12 shown in Table 43. [Table 43]

[001388] In Table 43, F represents a fluorine atom, Cl represents a chlorine atom, Br represents a bromine atom, and I represents an iodine atom.

[001389] For example, a compound in which X1, X2, and Zx are T1 shown in Table 43 in formula (TZF) represents the following compound.

[001390] According to the method mentioned above, it is possible to obtain the compounds TF-L001-1 to TCFF-L057-558.

[001391] Compounds TF-L001-1 to TCFF-L057-558 are compounds represented by the following formulas:

[Tabela 45]

[001392] where X1, X2, and RL represents any of the combinations L1 to L57 shown in Table 44 and Table 45, and Y represents a substituent corresponding to each of the substituents numbers 1 to 558. [Table 44]

[Table 45]

[001393] In Table 44 and Table 45, NO2 represents a nitro group, NH2 represents an amino group, NCO represents an isocyanate group, CO2H represents a carboxyl group, CO2CH3 represents a methoxycarbonyl group, CO2CH2CH3 represents an ethoxycarbonyl group, CO2 (CH2 ) 2CH3 represents a propyloxycarbonyl group, CO2CH (CH3) 2 represents an isopropyloxycarbonyl group, F represents a fluorine atom, Cl represents a chlorine atom, Br represents a bromine atom, I represents an iodine atom, COCI represents a group of formyl chloride, and COBr represents a group of formyl bromide.

[001394] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TF) (referred to as the compound TF ).

[001395] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001396] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001397] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001398] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001399] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001400] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001401] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in compound TF.

[001402] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TF.

[001403] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001404] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001405] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the number 1 to 558 substituents in compound TF.

[001406] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in compound TF.

[001407] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in compound TF.

[001408] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TF.

[001409] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001410] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001411] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the number 1 to 558 substituents in compound TF.

[001412] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001413] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001414] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001415] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001416] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001417] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001418] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001419] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001420] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001421] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001422] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001423] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001424] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001425] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and substituent Y is any of the number 1 to 558 substituents in compound TF.

[001426] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001427] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001428] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001429] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TF.

[001430] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001431] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001432] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001433] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001434] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001435] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001436] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001437] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001438] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001439] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001440] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001441] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001442] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001443] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and substituent Y is any one of the substituents number 1 to 558 in compound TF.

[001444] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001445] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001446] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001447] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TF.

[001448] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and substituent Y is any one of the substituents number 1 to 558 in compound TF.

[001449] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TF.

[001450] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TF.

[001451] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TC) (referred to as the TC compound ).

[001452] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001453] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001454] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001455] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001456] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001457] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001458] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001459] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001460] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001461] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001462] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001463] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in compound TC.

[001464] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001465] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001466] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001467] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001468] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001469] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001470] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001471] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001472] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001473] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001474] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001475] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001476] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001477] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001478] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001479] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001480] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001481] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001482] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001483] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001484] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001485] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001486] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001487] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001488] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001489] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001490] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001491] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001492] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001493] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001494] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001495] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001496] A tetrazolinone compound in which X1, X2, and RL are shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001497] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001498] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001499] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001500] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001501] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001502] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001503] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001504] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001505] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TC.

[001506] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TC.

[001507] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and substituent Y is any one of the substituents number 1 to 558 in compound TC.

[001508] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TB) (referred to as the TB compound ).

[001509] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TB compound.

[001510] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001511] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001512] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TB compound.

[001513] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001514] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001515] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TB compound.

[001516] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001517] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001518] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001519] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001520] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001521] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001522] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001523] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001524] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TB compound.

[001525] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and the Y substituent is any of the numbers 1 to 558 in the TB compound.

[001526] A tetrazolinone compound in which X1, X2, and RL are shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001527] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001528] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001529] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TB compound.

[001530] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001531] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001532] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001533] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001534] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001535] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and the Y substituent is any of the numbers 1 to 558 in the TB compound.

[001536] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001537] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001538] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001539] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001540] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001541] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TB.

[001542] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TB.

[001543] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001544] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001545] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and the substituent Y is any of the numbers 1 to 558 in the TB compound.

[001546] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001547] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001548] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001549] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001550] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001551] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001552] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001553] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001554] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001555] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and the substituent Y is any one of the numbers 1 to 558 in the TB compound.

[001556] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001557] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001558] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001559] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TB compound.

[001560] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001561] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TB compound.

[001562] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001563] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001564] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TB.

[001565] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and the Y substituent is any of the numbers 1 to 558 in a compound represented by the formula (TI) (referred to as the compound TI).

[001566] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001567] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001568] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001569] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001570] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001571] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001572] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001573] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001574] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001575] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001576] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001577] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001578] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001579] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001580] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in compound TI.

[001581] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TI compound.

[001582] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001583] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001584] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001585] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001586] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001587] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001588] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001589] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001590] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001591] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001592] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001593] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001594] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001595] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001596] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001597] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001598] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001599] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001600] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001601] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001602] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001603] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001604] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001605] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TI compound.

[001606] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001607] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001608] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001609] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001610] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001611] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001612] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001613] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001614] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001615] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001616] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001617] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TI compound.

[001618] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001619] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TI.

[001620] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001621] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TI.

[001622] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TM) (referred to as the TM compound) ).

[001623] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001624] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001625] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001626] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001627] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TM compound.

[001628] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001629] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001630] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001631] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001632] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the TM compound.

[001633] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001634] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001635] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001636] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001637] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001638] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001639] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001640] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001641] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001642] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001643] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001644] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001645] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001646] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001647] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001648] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001649] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001650] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001651] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001652] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001653] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001654] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001655] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001656] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any one of the substituents number 1 to 558 in the compound TM.

[001657] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001658] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001659] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001660] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001661] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001662] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001663] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001664] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001665] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001666] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001667] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001668] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001669] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001670] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001671] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001672] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001673] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001674] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001675] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001676] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001677] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TM compound.

[001678] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TM.

[001679] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TE) (referred to as the TE compound ).

[001680] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001681] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001682] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001683] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001684] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001685] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001686] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001687] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001688] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001689] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001690] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001691] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001692] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001693] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001694] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001695] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001696] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001697] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001698] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001699] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001700] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001701] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001702] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001703] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001704] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and the substituent Y is any of the numbers 1 to 558 in the TE compound.

[001705] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001706] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001707] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001708] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TE compound.

[001709] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001710] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001711] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001712] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001713] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001714] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and the substituent Y is any one of the substituents number 1 to 558 in the compound TE.

[001715] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001716] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001717] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001718] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001719] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001720] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001721] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001722] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001723] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001724] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and the Y substituent is any of the numbers 1 to 558 in the TE compound.

[001725] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001726] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001727] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001728] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001729] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001730] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001731] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001732] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in compound TE.

[001733] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001734] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and the substituent Y is any one of the substituents number 1 to 558 in the compound TE.

[001735] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TE.

[001736] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TV) (referred to as the TV compound ).

[001737] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001738] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001739] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001740] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001741] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001742] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001743] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001744] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001745] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001746] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001747] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001748] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001749] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001750] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001751] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001752] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001753] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001754] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001755] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001756] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001757] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001758] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001759] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001760] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001761] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001762] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001763] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001764] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001765] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001766] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001767] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001768] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001769] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001770] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001771] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001772] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001773] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001774] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001775] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001776] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001777] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001778] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001779] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 37, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001780] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001781] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001782] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001783] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001784] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001785] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001786] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001787] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001788] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001789] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001790] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TV compound.

[001791] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001792] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TV.

[001793] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TCY) (referred to as the TCY compound ).

[001794] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCY compound.

[001795] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001796] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001797] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001798] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001799] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001800] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001801] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001802] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001803] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 36, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001804] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001805] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001806] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001807] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001808] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001809] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001810] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001811] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001812] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001813] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001814] A tetrazolinone compound in which X1, X2, and RL are shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001815] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001816] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001817] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001818] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001819] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001820] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001821] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001822] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001823] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TCY compound.

[001824] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001825] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001826] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001827] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001828] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001829] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TCY compound.

[001830] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001831] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001832] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001833] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001834] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TCY compound.

[001835] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001836] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001837] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001838] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001839] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001840] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001841] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001842] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001843] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001844] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001845] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001846] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001847] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001848] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001849] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCY.

[001850] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TMO) (referred to as the TMO compound ).

[001851] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001852] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001853] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and the Y substituent is any of the numbers 1 to 558 in the TMO compound.

[001854] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001855] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001856] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001857] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001858] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the TMO compound.

[001859] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001860] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the TMO compound.

[001861] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001862] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001863] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and the Y substituent is any of the numbers 1 to 558 in the TMO compound.

[001864] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001865] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001866] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001867] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001868] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001869] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001870] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001871] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001872] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001873] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and the substituent Y is any of the numbers 1 to 558 in the TMO compound.

[001874] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001875] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001876] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001877] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001878] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001879] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001880] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001881] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001882] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001883] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and the substituent Y is any one of the numbers 1 to 558 in the TMO compound.

[001884] A tetrazolinone compound in which X1, X2, and RL are shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001885] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001886] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001887] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001888] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001889] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001890] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001891] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001892] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001893] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and the substituent Y is any one of the numbers 1 to 558 in the TMO compound.

[001894] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001895] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001896] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001897] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001898] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001899] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001900] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001901] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001902] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001903] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the substituent Y is any one of the numbers 1 to 558 in the TMO compound.

[001904] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001905] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001906] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMO compound.

[001907] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TMT) (referred to as the TMT compound ).

[001908] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001909] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001910] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001911] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the TMT compound.

[001912] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001913] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001914] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the TMT compound.

[001915] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the TMT compound.

[001916] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001917] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001918] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001919] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001920] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001921] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001922] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001923] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001924] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001925] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001926] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001927] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001928] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001929] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001930] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the TMT compound.

[001931] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001932] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001933] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001934] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001935] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001936] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001937] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001938] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001939] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001940] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001941] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001942] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001943] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001944] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001945] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 37, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001946] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001947] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001948] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001949] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any one of the substituents number 1 to 558 in the TMT compound.

[001950] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001951] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001952] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001953] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001954] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001955] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001956] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001957] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001958] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001959] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001960] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001961] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and the Y substituent is any of the number 1 to 558 substituents in the TMT compound.

[001962] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001963] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TMT compound.

[001964] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TCF) (referred to as the TCF compound ).

[001965] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001966] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001967] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001968] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001969] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001970] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001971] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001972] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001973] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001974] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001975] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001976] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001977] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001978] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001979] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001980] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001981] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001982] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001983] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001984] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001985] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001986] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001987] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001988] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001989] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001990] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001991] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001992] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001993] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001994] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001995] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001996] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001997] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001998] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[001999] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and substituent Y is any one of the substituents number 1 to 558 in the TCF compound.

[002000] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and the Y substituent is any of the substituents number 1 to 558 in the TCF compound.

[002001] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002002] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002003] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any one of the substituents number 1 to 558 in the TCF compound.

[002004] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002005] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002006] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002007] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002008] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002009] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002010] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002011] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002012] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002013] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002014] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002015] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002016] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002017] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002018] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002019] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002020] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the TCF compound.

[002021] A tetrazolinone compound in which X1, X2, and RL are L1 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in a compound represented by the formula (TCFF) (referred to as the TCFF compound ).

[002022] A tetrazolinone compound in which X1, X2, and RL are L2 shown in Table 44, and the Y substituent is any of the numbers 1 to 558 in the TCFF compound.

[002023] A tetrazolinone compound in which X1, X2, and RL are L3 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002024] A tetrazolinone compound in which X1, X2, and RL are L4 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002025] A tetrazolinone compound in which X1, X2, and RL are L5 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002026] A tetrazolinone compound in which X1, X2, and RL are L6 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002027] A tetrazolinone compound in which X1, X2, and RL are L7 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002028] A tetrazolinone compound in which X1, X2, and RL are L8 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002029] A tetrazolinone compound in which X1, X2, and RL are L9 shown in Table 44, and the Y substituent is any of the substituents number 1 to 558 in the TCFF compound.

[002030] A tetrazolinone compound in which X1, X2, and RL are L10 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002031] A tetrazolinone compound in which X1, X2, and RL are L11 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002032] A tetrazolinone compound in which X1, X2, and RL are L12 shown in Table 44, and the substituent Y is any of the numbers 1 to 558 in the TCFF compound.

[002033] A tetrazolinone compound in which X1, X2, and RL are L13 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002034] A tetrazolinone compound in which X1, X2, and RL are L14 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002035] A tetrazolinone compound in which X1, X2, and RL are L15 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the compound TCFF.

[002036] A tetrazolinone compound in which X1, X2, and RL are L16 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002037] A tetrazolinone compound in which X1, X2, and RL are L17 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002038] A tetrazolinone compound in which X1, X2, and RL are L18 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002039] A tetrazolinone compound in which X1, X2, and RL are L19 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002040] A tetrazolinone compound in which X1, X2, and RL are L20 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002041] A tetrazolinone compound in which X1, X2, and RL are L21 shown in Table 44, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002042] A tetrazolinone compound in which X1, X2, and RL are L22 shown in Table 44, and the Y substituent is any of the numbers 1 to 558 in the TCFF compound.

[002043] A tetrazolinone compound in which X1, X2, and RL are L23 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002044] A tetrazolinone compound in which X1, X2, and RL are L24 shown in Table 44, and substituent Y is any one of the substituents number 1 to 558 in the compound TCFF.

[002045] A tetrazolinone compound in which X1, X2, and RL are L25 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002046] A tetrazolinone compound in which X1, X2, and RL are L26 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002047] A tetrazolinone compound in which X1, X2, and RL are L27 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002048] A tetrazolinone compound in which X1, X2, and RL are L28 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002049] A tetrazolinone compound in which X1, X2, and RL are L29 shown in Table 44, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002050] A tetrazolinone compound in which X1, X2, and RL are L30 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002051] A tetrazolinone compound in which X1, X2, and RL are L31 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002052] A tetrazolinone compound in which X1, X2, and RL are L32 shown in Table 45, and the Y substituent is any of the numbers 1 to 558 in the TCFF compound.

[002053] A tetrazolinone compound in which X1, X2, and RL are L33 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002054] A tetrazolinone compound in which X1, X2, and RL are L34 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002055] A tetrazolinone compound in which X1, X2, and RL are L35 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002056] A tetrazolinone compound in which X1, X2, and RL are L36 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002057] A tetrazolinone compound in which X1, X2, and RL are L37 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002058] A tetrazolinone compound in which X1, X2, and RL are L38 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002059] A tetrazolinone compound in which X1, X2, and RL are L39 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002060] A tetrazolinone compound in which X1, X2, and RL are L40 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002061] A tetrazolinone compound in which X1, X2, and RL are L41 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002062] A tetrazolinone compound in which X1, X2, and RL are L42 shown in Table 45, and the substituent Y is any one of the numbers 1 to 558 in the TCFF compound.

[002063] A tetrazolinone compound in which X1, X2, and RL are L43 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002064] A tetrazolinone compound in which X1, X2, and RL are L44 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002065] A tetrazolinone compound in which X1, X2, and RL are L45 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002066] A tetrazolinone compound in which X1, X2, and RL are L46 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002067] A tetrazolinone compound in which X1, X2, and RL are L47 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002068] A tetrazolinone compound in which X1, X2, and RL are L48 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002069] A tetrazolinone compound in which X1, X2, and RL are L49 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002070] A tetrazolinone compound in which X1, X2, and RL are L50 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002071] A tetrazolinone compound in which X1, X2, and RL are L51 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002072] A tetrazolinone compound in which X1, X2, and RL are L52 shown in Table 45, and the Y substituent is any of the numbers 1 to 558 in the TCFF compound.

[002073] A tetrazolinone compound in which X1, X2, and RL are L53 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002074] A tetrazolinone compound in which X1, X2, and RL are L54 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002075] A tetrazolinone compound in which X1, X2, and RL are L55 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002076] A tetrazolinone compound in which X1, X2, and RL are L56 shown in Table 45, and the substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002077] A tetrazolinone compound in which X1, X2, and RL are L57 shown in Table 45, and substituent Y is any of the substituents number 1 to 558 in the compound TCFF.

[002078] For example, a compound in which X1, X2, and RL are L1 shown in Table 44, and Y is a number 1 substituent in the formula (TF) represents the following compound.

[002079] Examples of the present control agent include:

[002080] a pest control composition comprising any of the present compound 1 to the present compound 221, and protioconazole in a ratio of 0.1: 1;

[002081] a pest control composition comprising any one of the present compound 1 to the present compound 221, and protioconazole in a 1: 1 ratio;

[002082] a pest control composition comprising any of the present compound 1 to the present compound 221, and protioconazole in a 10: 1 ratio;

[002083] a pest control composition comprising any of the present compound 1 to the present compound 221, and bromuconazole in a ratio of 0.1: 1;

[002084] a pest control composition comprising any one of the present compound 1 to the present compound 221, and bromuconazole in a 1: 1 ratio;

[002085] a pest control composition comprising any of the present compound 1 to the present compound 221, and bromuconazole in a 10: 1 ratio;

[002086] a pest control composition comprising any of the present compound 1 to the present compound 221, and metconazole in a ratio of 0.1: 1;

[002087] a pest control composition comprising any of the present compound 1 to the present compound 221, and metconazole in a 1: 1 ratio;

[002088] a pest control composition comprising any of the present compound 1 to the present compound 221, and metconazole in a 10: 1 ratio;

[002089] a pest control composition comprising any of the present compound 1 to the present compound 221, and tebuconazole in a ratio of 0.1: 1;

[002090] a pest control composition comprising any of the present compound 1 to the present compound 221, and tebuconazole in a 1: 1 ratio;

[002091] a pest control composition comprising any of the present compound 1 to the present compound 221, and tebuconazole in a 10: 1 ratio;

[002092] a pest control composition comprising any of the present compound 1 to the present compound 221, and tetraconazole in a ratio of 0.1: 1;

[002093] a pest control composition comprising any of the present compound 1 to the present compound 221, and tetraconazole in a 1: 1 ratio;

[002094] a pest control composition comprising any one of the present compound 1 to the present compound 221, and tetraconazole in a 10: 1 ratio;

[002095] a pest control composition comprising any one of the present compound 1 to the present compound 221, and cyproconazole in a ratio of 0.1: 1;

[002096] a pest control composition comprising any of the present compound 1 to the present compound 221, and cyproconazole in a 1: 1 ratio;

[002097] a pest control composition comprising any one of the present compound 1 to the present compound 221, and cyproconazole in a 10: 1 ratio;

[002098] a pest control composition comprising any of the present compound 1 to the present compound 221, and flusilazole in a ratio of 0.1: 1;

[002099] a pest control composition comprising any of the present compound 1 to the present compound 221, and flusilazole in a 1: 1 ratio;

[002100] a pest control composition comprising any of the present compound 1 to the present compound 221, and flusilazole in a 10: 1 ratio;

[002101] a pest control composition comprising any one of the present compound 1 to the present compound 221, and prochloraz in a ratio of 0.1: 1;

[002102] a pest control composition comprising any one of the present compound 1 to the present compound 221, and prochloraz in a 1: 1 ratio;

[002103] a pest control composition comprising any one of the present compound 1 to the present compound 221, and prochloraz in a 10: 1 ratio;

[002104] a pest control composition comprising any of the present compound 1 to the present compound 221, and azoxystrobin in a ratio of 0.1: 1;

[002105] a pest control composition comprising any of the present compound 1 to the present compound 221, and azoxystrobin in a 1: 1 ratio;

[002106] a pest control composition comprising any of the present compound 1 to the present compound 221, and azoxystrobin in a 10: 1 ratio;

[002107] a pest control composition comprising any of the present compound 1 to the present compound 221, and pyraclostrobin in a ratio of 0.1: 1;

[002108] a pest control composition comprising any one of the present compound 1 to the present compound 221, and pyraclostrobin in a 1: 1 ratio;

[002109] a pest control composition comprising any of the present compound 1 to the present compound 221, and pyraclostrobin in a 10: 1 ratio;

[002110] a pest control composition comprising any of the present compound 1 to the present compound 221, and picoxystrobin in a ratio of 0.1: 1;

[002111] a pest control composition comprising any of the present compound 1 to the present compound 221, and picoxystrobin in a 1: 1 ratio;

[002112] a pest control composition comprising any of the present compound 1 to the present compound 221, and picoxystrobin in a 10: 1 ratio;

[002113] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fluoxastrobin in a ratio of 0.1: 1;

[002114] a pest control composition comprising any of the present compound 1 to the present compound 221, and fluoxastrobin in a 1: 1 ratio;

[002115] a pest control composition comprising any of the present compound 1 to the present compound 221, and fluoxastrobin in a 10: 1 ratio;

[002116] a pest control composition comprising any of the present compound 1 to the present compound 221, and trifioxystrobin in a ratio of 0.1: 1;

[002117] a pest control composition comprising any one of the present compound 1 to the present compound 221, and trifioxystrobin in a 1: 1 ratio;

[002118] a pest control composition comprising any of the present compound 1 to the present compound 221, and trifioxystrobin in a 10: 1 ratio;

[002119] a pest control composition comprising any of the present compound 1 to the present compound 221, and mandestrobin in a ratio of 0.1: 1;

[002120] a pest control composition comprising any one of the present compound 1 to the present compound 221, and mandestrobin in a 1: 1 ratio;

[002121] a pest control composition comprising any one of the present compound 1 to the present compound 221, and mandestrobin in a 10: 1 ratio;

[002122] a pest control composition comprising any of the present compound 1 to the present compound 221, and fluoxastrobin in a ratio of 0.1: 1;

[002123] a pest control composition comprising any of the present compound 1 to the present compound 221, and fluoxastrobin in a 1: 1 ratio;

[002124] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fluoxastrobin in a 10: 1 ratio;

[002125] a pest control composition comprising any of the present compound 1 to the present compound 221, and bixafen in a ratio of 0.1: 1;

[002126] a pest control composition comprising any of the present compound 1 to the present compound 221, and bixafen in a 1: 1 ratio;

[002127] a pest control composition comprising any of the present compound 1 to the present compound 221, and bixafen in a 10: 1 ratio;

[002128] a pest control composition comprising any one of the present compound 1 to the present compound 221, and isopyrazam in a ratio of 0.1: 1;

[002129] a pest control composition comprising any of the present compound 1 to the present compound 221, and isopyrazam in a 1: 1 ratio;

[002130] a pest control composition comprising any of the present compound 1 to the present compound 221, and isopyrazam in a 10: 1 ratio;

[002131] a pest control composition comprising any of the present compound 1 to the present compound 221, and fluopyram in a ratio of 0.1: 1;

[002132] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fluopy in a 1: 1 ratio;

[002133] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fluopy in a 10: 1 ratio;

[002134] a pest control composition comprising any of the present compound 1 to the present compound 221, and pentiopirad in a ratio of 0.1: 1;

[002135] a pest control composition comprising any one of the present compound 1 to the present compound 221, and pentiopirad in a 1: 1 ratio;

[002136] a pest control composition comprising any of the present compound 1 to the present compound 221, and pentiopirad in a 10: 1 ratio;

[002137] a pest control composition comprising any one of the present compound 1 to the present compound 221, and benzovindiflupir in a ratio of 0.1: 1;

[002138] a pest control composition comprising any of the present compound 1 to the present compound 221, and benzovindiflupir in a 1: 1 ratio;

[002139] a pest control composition comprising any of the present compound 1 to the present compound 221, and benzovindiflupir in a 10: 1 ratio;

[002140] a pest control composition comprising any of the present compound 1 to the present compound 221, and fluxpyroxade in a ratio of 0.1: 1;

[002141] a pest control composition comprising any of the present compound 1 to the present compound 221, and fluxpyroxade in a 1: 1 ratio;

[002142] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fluxpyroxade in a 10: 1 ratio;

[002143] a pest control composition comprising any one of the present compound 1 to the present compound 221, and boscalide in a ratio of 0.1: 1;

[002144] a pest control composition comprising any one of the present compound 1 to the present compound 221, and boscalide in a 1: 1 ratio;

[002145] a pest control composition comprising any one of the present compound 1 to the present compound 221, and boscalide in a 10: 1 ratio;

[002146] a pest control composition comprising any of the present compound 1 to the present compound 221, and N- [2- (3,4-difluorophenyl) phenyl] -3-trifluoromethylpyrazine-2-carboxylic acid amide in a relationship 0.1: 1;

[002147] a pest control composition comprising any of the present compound 1 to the present compound 221, and N- [2- (3,4-difluorophenyl) phenyl] -3-trifluoromethylpyrazine-2-carboxylic acid amide in a relationship 1: 1;

[002148] a pest control composition comprising any of the present compound 1 to the present compound 221, and N- [2- (3,4-difluorophenyl) phenyl] -3-trifluoromethylpyrazine-2-carboxylic acid amide in a relationship 10: 1;

[002149] a pest control composition comprising any of the present compound 1 to the present compound 221, and acid amide (R) - (-) - N- (1,1,3-trimethylindan-4-yl) -1 -methyl-3-difluoromethylpyrazole-4-carboxylic in a ratio of 0.1: 1;

[002150] a pest control composition comprising any one of the present compound 1 to the present compound 221, and acid amide (R) - (-) - N- (1,1,3-trimethylindan-4-yl) -1 -methyl-3-difluoromethylpyrazole-4-carboxylic in a 1: 1 ratio;

[002151] a pest control composition comprising any of the present compound 1 to the present compound 221, and acid amide (R) - (-) - N- (1,1,3-trimethylindan-4-yl) -1 -methyl-3-difluoromethylpyrazole-4-carboxylic in a 10: 1 ratio;

[002152] a pest control composition comprising any of the present compound 1 to the present compound 221, and 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine in a ratio of 0.1 :1;

[002153] a pest control composition comprising any one of the present compound 1 to the present compound 221, and 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine in a 1: 1 ratio ;

[002154] a pest control composition comprising any one of the present compound 1 to the present compound 221, and 3-chloro-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine in a 10: 1 ratio ;

[002155] a pest control composition comprising any one of the present compound 1 to the present compound 221, and 3-cyano-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine in a ratio of 0.1 :1;

[002156] a pest control composition comprising any one of the present compound 1 to the present compound 221, and 3-cyano-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine in a 1: 1 ratio ;

[002157] a pest control composition comprising any one of the present compound 1 to the present compound 221, and 3-cyano-4- (2,6-difluorophenyl) -6-methyl-5-phenylpyridazine in a 10: 1 ratio ;

[002158] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fenpropimorph in a ratio of 0.1: 1;

[002159] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fenpropimorph in a 1: 1 ratio;

[002160] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fenpropimorph in a 10: 1 ratio;

[002161] a pest control composition comprising any of the present compound 1 to the present compound 221, and phenpropidine in a ratio of 0.1: 1;

[002162] a pest control composition comprising any of the present compound 1 to the present compound 221, and phenpropidine in a 1: 1 ratio;

[002163] a pest control composition comprising any of the present compound 1 to the present compound 221, and phenpropidine in a 10: 1 ratio;

[002164] a pest control composition comprising any of the present compound 1 to the present compound 221, and spiroxamine in a ratio of 0.1: 1;

[002165] a pest control composition comprising any of the present compound 1 to the present compound 221, and spiroxamine in a 1: 1 ratio;

[002166] a pest control composition comprising any of the present compound 1 to the present compound 221, and spiroxamine in a 10: 1 ratio;

[002167] a pest control composition comprising any of the present compound 1 to the present compound 221, and cyprodinil in a ratio of 0.1: 1;

[002168] a pest control composition comprising any of the present compound 1 to the present compound 221, and cyprodinil in a 1: 1 ratio;

[002169] a pest control composition comprising any of the present compound 1 to the present compound 221, and cyprodinil in a 10: 1 ratio;

[002170] a pest control composition comprising any one of the present compound 1 to the present compound 221, and pyrimethanil in a ratio of 0.1: 1;

[002171] a pest control composition comprising any of the present compound 1 to the present compound 221, and pyrimethanil in a 1: 1 ratio;

[002172] a pest control composition comprising any of the present compound 1 to the present compound 221, and pyrimethanil in a 10: 1 ratio;

[002173] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fludioxonil in a ratio of 0.1: 1;

[002174] a pest control composition comprising any one of the present compound 1 to the present compound 221, and fludioxonil in a 1: 1 ratio;

[002175] a pest control composition comprising any of the present compound 1 to the present compound 221, and fludioxonil in a 10: 1 ratio;

[002176] a pest control composition comprising any one of the present compound 1 to the present compound 221, and procymidone in a ratio of 0.1: 1;

[002177] a pest control composition comprising any of the present compound 1 to the present compound 221, and procymidone in a 1: 1 ratio;

[002178] a pest control composition comprising any of the present compound 1 to the present compound 221, and procymidone in a 10: 1 ratio;

[002179] a pest control composition comprising any one of the present compound 1 to the present compound 221, and iprodione in a ratio of 0.1: 1;

[002180] a pest control composition comprising any one of the present compound 1 to the present compound 221, and iprodione in a 1: 1 ratio;

[002181] a pest control composition comprising any one of the present compound 1 to the present compound 221, and iprodione in a 10: 1 ratio;

[002182] a pest control composition comprising any of the present compound 1 to the present compound 221, and thiophanate-methyl in a ratio of 0.1: 1;

[002183] a pest control composition comprising any one of the present compound 1 to the present compound 221, and thiophanate-methyl in a 1: 1 ratio;

[002184] a pest control composition comprising any one of the present compound 1 to the present compound 221, and thiophanate-methyl in a 10: 1 ratio;

[002185] a pest control composition comprising any one of the present compound 1 to the present compound 221, and carbendazim in a ratio of 0.1: 1;

[002186] a pest control composition comprising any one of the present compound 1 to the present compound 221, and carbendazim in a 1: 1 ratio;

[002187] a pest control composition comprising any of the present compound 1 to the present compound 221, and carbendazim in a 10: 1 ratio;

[002188] a pest control composition comprising any of the present compound 1 to the present compound 221, and dietophenacarb in a ratio of 0.1: 1;

[002189] a pest control composition comprising any one of the present compound 1 to the present compound 221, and dietophenacarb in a 1: 1 ratio;

[002190] a pest control composition comprising any one of the present compound 1 to the present compound 221, and dietophenacarb in a 10: 1 ratio;

[002191] a pest control composition comprising any of the present compound 1 to the present compound 221, and phenpyrazamine in a ratio of 0.1: 1;

[002192] a pest control composition comprising any of the present compound 1 to the present compound 221, and phenpyrazamine in a 1: 1 ratio;

[002193] a pest control composition comprising any of the present compound 1 to the present compound 221, and phenpyrazamine in a 10: 1 ratio;

[002194] a pest control composition comprising any of the present compound 1 to the present compound 221, and chlorothalonil in a ratio of 0.1: 1;

[002195] a pest control composition comprising any of the present compound 1 to the present compound 221, and chlorothalonil in a 1: 1 ratio;

[002196] a pest control composition comprising any of the present compound 1 to the present compound 221, and chlorothalonil in a 10: 1 ratio;

[002197] a pest control composition comprising any of the present compound 1 to the present compound 221, and manzeb in a ratio of 0.1: 1;

[002198] a pest control composition comprising any of the present compound 1 to the present compound 221, and manzeb in a 1: 1 ratio;

[002199] a pest control composition comprising any of the present compound 1 to the present compound 221, and manzeb in a 10: 1 ratio;

[002200] a pest control composition comprising any one of the present compound 1 to the present compound 221, and folpet in a ratio of 0.1: 1;

[002201] a pest control composition comprising any one of the present compound 1 to the present compound 221, and folpet in a 1: 1 ratio;

[002202] a pest control composition comprising any of the present compound 1 to the present compound 221, and folpet in a 10: 1 ratio;

[002203] a pest control composition comprising any one of the present compound 1 to the present compound 221, and met in a ratio of 0.1: 1;

[002204] a pest control composition comprising any one of the present compound 1 to the present compound 221, and met in a 1: 1 ratio;

[002205] a pest control composition comprising any one of the present compound 1 to the present compound 221, and met in a 10: 1 ratio;

[002206] a pest control composition comprising any of the present compound 1 to the present compound 221, and clothianidin in a 1: 1 ratio;

[002207] a pest control composition comprising any one of the present compound 1 to the present compound 221, and clothianidin in a 1:10 ratio;

[002208] a pest control composition comprising any of the present compound 1 to the present compound 221, and clothianidin in a 1:50 ratio;

[002209] a pest control composition comprising any of the present compound 1 to the present compound 221, and imidacloprid in a 1: 1 ratio;

[002210] a pest control composition comprising any one of the present compound 1 to the present compound 221, and imidacloprid in a 1:10 ratio;

[002211] a pest control composition comprising any one of the present compound 1 to the present compound 221, and imidacloprid in a 1:50 ratio;

[002212] a pest control composition comprising any of the present compound 1 to the present compound 221, and thiamethoxam in a 1: 1 ratio;

[002213] a pest control composition comprising any of the present compound 1 to the present compound 221, and thiamethoxam in a 1:10 ratio;

[002214] a pest control composition comprising any one of the present compound 1 to the present compound 221, and thiamethoxam in a 1:50 ratio;

[002215] a pest control composition comprising any of the present compound 1 to the present compound 221, and dinotefuran in a 1: 1 ratio;

[002216] a pest control composition comprising any one of the present compound 1 to the present compound 221, and dinotefuran in a 1:10 ratio;

[002217] a pest control composition comprising any one of the present compound 1 to the present compound 221, and dinotefuran in a 1:50 ratio;

[002218] a pest control composition comprising any of the present compound 1 to the present compound 221, and sulfoxaflor in a 1: 1 ratio;

[002219] a pest control composition comprising any of the present compound 1 to the present compound 221, and sulfoxaflor in a 1:10 ratio;

[002220] a pest control composition comprising any one of the present compound 1 to the present compound 221, and sulfoxaflor in a 1:50 ratio;

[002221] a pest control composition comprising any one of the present compound 1 to the present compound 221, and chlorantraniliprol in a 1: 1 ratio;

[002222] a pest control composition comprising any of the present compound 1 to the present compound 221, and chloranthranilprol in a 1:10 ratio;

[002223] a pest control composition comprising any of the present compound 1 to the present compound 221, and chloranthranilprol in a 1:50 ratio;

[002224] a pest control composition comprising any one of the present compound 1 to the present compound 221, and cyantraniliprol in a 1: 1 ratio;

[002225] a pest control composition comprising any one of the present compound 1 to the present compound 221, and cyantraniliprol in a 1:10 ratio;

[002226] a pest control composition comprising any one of the present compound 1 to the present compound 221, and cyantraniliprol in a 1:50 ratio;

[002227] a pest control composition comprising any of the present compound 1 to the present compound 221, and cyclaniliprol in a 1: 1 ratio;

[002228] a pest control composition comprising any of the present compound 1 to the present compound 221, and cyclaniliprol in a 1:10 ratio;

[002229] a pest control composition comprising any one of the present compound 1 to the present compound 221, and cyclaniliprol in a 1:50 ratio;

[002230] a pest control composition comprising any of the present compound 1 to the present compound 221, and abamectin in a 1: 1 ratio;

[002231] a pest control composition comprising any one of the present compound 1 to the present compound 221, and abamectin in a 1:10 ratio;

[002232] a pest control composition comprising any of the present compound 1 to the present compound 221, and abamectin in a 1:50 ratio;

[002233] a pest control composition comprising any of the present compound 1 to the present compound 221, and 4-oxo-4- (2-phenylethyl) aminobutyric acid in a 5: 1 ratio;

[002234] a pest control composition comprising any of the present compound 1 to the present compound 221, and 4-oxo-4- (2-phenylethyl) aminobutyric acid in a 1:10 ratio;

[002235] a pest control composition comprising any of the present compound 1 to the present compound 221, and 4-oxo-4- (2-phenylethyl) aminobutyric acid in a 1:50 ratio;

[002236] a pest control composition comprising any of the present compound 1 to the present compound 221, and methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carbonate in a 5: 1 ratio;

[002237] a pest control composition comprising any of the present compound 1 to the present compound 221, and methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carbonate in a 1:10 ratio;

[002238] a pest control composition comprising any of the present compound 1 to the present compound 221, and methyl 5- (trifluoromethyl) benzo [b] thiophene-2-carbonate in a 1:50 ratio;

[002239] a pest control composition comprising any one of the present compound 1 to the present compound 221, and 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylic acid in a 5: 1 ratio;

[002240] a pest control composition comprising any of the present compound 1 to the present compound 221, and 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylic acid in a 1:10 ratio; and

[002241] a pest control composition comprising any one of the present compound 1 to the present compound 221, and 5- (trifluoromethyl) benzo [b] thiophene-2-carboxylic acid in a 1:50 ratio.

[002242] Formulation Examples will be shown below. The parts are by weight.

Formulation Example 1

[002243] Fifty parts (50 parts) of any of the present compounds 1 to 221, 3 parts of calcium ligninosulfoate, 2 parts of laurylmagnesium sulfate, and 45 parts of synthetic hydrated silicon oxide are carefully crushed and mixed to obtain each formulation.

Formulation Example 2

[002244] Twenty parts (20 parts) of any of the present compounds 1 to 221 and 1.5 part of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture was finely ground by a wet grinding method. Then 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate are added to it and 10 parts of propylene glycol are also added, followed by stirring and mixing to obtain each formulation.

Formulation Example 3

[002245] Two parts (2 parts) of any of the present compounds 1 to 221, 88 parts of kaolin clay, and 10 parts of talc are carefully crushed and mixed to obtain each formulation.

Formulation Example 4

[002246] Five parts (5 parts) of any of the present compounds 1 to 221, 14 parts of polyoxyethylene styrene phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are carefully crushed and mixed to obtain each formulation.

Formulation Example 5

[002247] Two parts (2 parts) of any of the present compounds 1 to 221, 1 part of synthetic hydrated silicon oxide, 2 parts of calcium ligninsulfoate, 30 parts of bentonite, and 65 parts of kaolin clay are carefully ground and mixed. After adding water, the mixture is carefully kneaded and granulated and dried again to obtain each formulation.

Formulation Example 6

[002248] Ten parts (10 parts) of any of the present compounds 1 to 221, 35 parts of white carbon, containing 50 parts of an ammonium salt of polyoxyethylene alkyl ether sulfate, and 55 parts of water were finely ground by a wet grinding method to obtain each formulation.

[002249] The following Test Examples will show that the present compounds are useful for the control of plant diseases.

[002250] The control effect was assessed by visual observation of the area of injury points on each of the test plants at the time of investigation, and comparing the area of injury points on the plant treated with the present control compound with that on an untreated plant. The untreated plant is a plant tested under the same conditions as the Test Examples, except that the leaf or foliage application of a solution of a formulation containing the present compound with water is not carried out.

Test Example 1

[002251] Each of the plastic pots was filled with sandy clay and barley (cultivar. MIKAMO GOLDEN) was sown and grown in a greenhouse for 7 days, the present compound 1 was diluted with water to adjust to a predetermined concentration of 3, 1 ppm. The diluted solution obtained was sprayed on the stems and leaves of the barley so that it was sufficiently adhered to the surface of the leaves of the barley. After vaporization, the plant was dried by air. After 2 days, an aqueous suspension containing barley spot fungus spores (Pirenophora teres) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to rest for 3 days in a greenhouse at 23 ° C during the day and 20 ° C during the night under high humidity conditions and grown in a greenhouse for 7 days, and then the injury spots was investigated. As a result, it was found that the area of lesion spots on a plant treated with the present compound 1 was 30% or less than that on an untreated plant.

Test Example 2

[002252] Each of the plastic pots was filled with sandy clay and cucumber (cultivar.SAGAMI HANJIRO) was sown and cultivated in a greenhouse for 12 days. Each of the present compounds 35, 40, 61, 64, 92, 100, 101, 107, 110, 143, 148, 167 to 169, 172 to 174, 176 to 180, 206, 209, 210, and 215 to 217 were diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the stems and leaves of the cucumber so that it was sufficiently adhered to the surface of the leaves of the cucumber. After vaporization, the plant was air-dried and then inoculated by sprinkling with fungus spores from the dusty cucumber mold (Sphaerotheca fuliginea, a Qol-resistant strain in which, among the genes encoding cytochrome b, the amino acid residue in position 143 of cytochrome b is mutated from glycine to alanine). After inoculation, the plant was grown in a greenhouse at 24 ° C during the day and 20 ° C at night for 8 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 35, 40, 61, 64, 92, 100, 101, 107, 110, 143, 148, 167 to 169, 172 to 174, 176 to 180, 206, 209, 210, and 215 to 217 was 30% or less than that on an untreated plant.

Test Example 3

[002253] Each of the plastic pots was filled with sandy clay and rice (cultivar: NIHONBARE) was sown and cultivated in a greenhouse for 20 days. Each of the present compounds 2, 4, 6, 14, 18, 39, 40, 62, 65, 98, 109, 117, 119, 120, 122, 125, 131, 136, 137, 139 to 141, 153, and 157 was diluted with water to adjust to a predetermined concentration of 500 ppm. The diluted solutions obtained were sprayed on stems and leaves so that they are sufficiently adhered to the surface of the rice leaves. After spraying, the plant was air-dried and subjected to spray treatment and the rice seedling (cultivar: NIHONBARE) infected with the rice blast fungus (Magnaporthe grisea) allowed to rest for 6 days at 24 ° C during the day and 20 ° C overnight under high humidity condition, while in contact with each other, and then the lesion spot area was investigated. As a result, the areas of injury in a plant treated with the present compounds 2, 4, 6, 14, 18, 39, 40, 62, 65, 98, 109, 117, 119, 120, 122, 125, 131, 136, 137, 139 to 141, 153, and 157 were 30% or less with respect to the area of injury in the untreated plant.

Test Example 4

[002254] Each of the plastic pots was filled with sandy clay and rice (cultivar: NIHONBARE) was sown and cultivated in a greenhouse for 20 days. Each of the present compounds 1, 5, 7, 8, 11, 13, 15, 19, 21, 37, 46, 48, 49, 55 to 58, 60, 66, 67, 69, 70, 72 to 74, 84 , 86, 87, 91, 92, 94, 97, 101, 103, 106, 110, 112, 116, 118, 124, 126, 128, 132, 134, 138, 144, 149, 150, 151, 152, 167 , 169 to 174, 176, 178 to 180, 209, 210, and 215 to 217 were diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solutions obtained were sprayed on stems and leaves so that they are sufficiently adhered to the surface of the rice leaves. After spraying, the plant was air-dried and subjected to a spray treatment and the rice seedling (cultivar: NIHONBARE) infected with the rice blast fungus (Magnaporthe grisea) was allowed to rest for 6 days at 24 ° C during the day and 20 ° C overnight under high humidity condition, while in contact with each other, and then the area of lesion spots was investigated. As a result, the lesion areas on a plant treated with the present compounds 1, 5, 7, 8, 11, 13, 15, 19, 21, 37, 46, 48, 49, 55 to 58, 60, 66, 67, 69, 70, 72 to 74, 84, 86, 87, 91, 92, 94, 97, 101, 103, 106, 110, 112, 116, 118, 124, 126, 128, 132, 134, 138, 144, 149, 150, 151, 152, 167, 169 to 174, 176, 178 to 180, 209, 210, and 215 to 217 were 30% or less with respect to the area of injury in the untreated plant.

Test Example 5

[002255] Each of the plastic pots was filled with sandy clay and wheat (cultivar: SHIROGANE) was sown and cultivated in a greenhouse for 9 days. Each of the present compounds 4, 5, 11, 13, 14, 23, 39, 48, 65, 66, 98, 101, 116, 117, 119, 120, 122, 125, 126, 131, 137, 139 to 141 , and 157 was diluted with water to adjust to a predetermined concentration of 500 ppm. The diluted solution obtained was sprayed onto the wheat stems and leaves so that it is sufficiently adhered to the surface of the wheat leaves. After vaporization, the plant was air-dried and cultivated at 20 ° C for 5 days under lighting, and then inoculated by spraying with wheat rust fungus spores (Puccinia recondita). After inoculation, the plant was allowed to rest at 23 ° C for a day in the dark and high humidity condition, and grown under lighting at 20 ° C for 8 days, and then the lesion spot area was investigated. As a result, it was found that the area of lesion spots on the plant treated with each of the present compounds 4, 5, 11, 13, 14, 23, 39, 48, 65, 66, 98, 101, 116, 117 , 119, 120, 122, 125, 126, 131, 137, 139 to 141, and 157 was 30% or less than that on an untreated plant.

Test Example 6

[002256] Each of the plastic pots was filled with sandy clay and wheat (cultivar: SHIROGANE) was sown and cultivated in a greenhouse for 9 days. Each of the present compounds 2, 6 to 8, 19, 20, 26, 37, 40 to 44, 46, 49, 50, 53, 55 to 58, 60, 67 to 70, 72 to 74, 92, 93, 100 , 102, 106, 107, 112, 118, 121, 128, 134, 136, 138, 143, 148, 153, 158, 163, 164, 166, 169 to 172, 174, 177 to 181, 209, 210, 215 , and 217 was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the wheat stems and leaves so that it was sufficiently adhered to the surface of the wheat leaves. After vaporization, the plant was air-dried and cultivated at 20 ° C for 5 days under lighting, and then inoculated by spraying with wheat rust fungus spores (Puccinia recondita). After inoculation, the plant was allowed to rest at 23 ° C for a day in the dark and high humidity condition, and grown under lighting at 20 ° C for 8 days, and then the lesion spot area was investigated. As a result, it was discovered that the area of lesion spots on the plant treated with each of the present compounds 2, 6 to 8, 19, 20, 26, 37, 40 to 44, 46, 49, 50, 53, 55 to 58, 60, 67 to 70, 72 to 74, 92, 93, 100, 102, 106, 107, 112, 118, 121, 128, 134, 136, 138, 143, 148, 153, 158, 163, 164 , 166, 169 to 172, 174, 177 to 181, 209, 210, 215, and 217 was 30% or less than that on an untreated plant.

Test Example 7

[002257] Each of the plastic pots was filled with sandy clay and barley (cultivar. MIKAMO GOLDEN) was sown and cultivated in a greenhouse for 7 days. Each of the present compounds 1 to 8, 10, 11, 13 to 16, 18 to 27, 29, 31, 35, 37 to 50, 52 to 57, 59 to 75, 77, 80, 81, 83 to 88, 90 at 94, 96 to 104, 107, 109, 110, 112 to 114, 116 to 122, 124 to 129, 131 to 144, 147 to 164, and 165 was diluted with water to adjust to a predetermined concentration of 500 ppm. The diluted solution obtained was sprayed on the stems and leaves of the barley so that they are sufficiently adhered to the surface of the leaves of the barley. After vaporization, the plant was dried by air. After 2 days, an aqueous suspension containing barley spot fungus spores (Pirenophora teres) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to rest for 3 days in a greenhouse at 23 ° C during the day and 20 ° C during the night under high humidity conditions and grown in a greenhouse for 7 days, and then the injury spots was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 1 to 8, 10, 11, 13 to 16, 18 to 27, 29, 31, 35, 37 to 50, 52 to 57, 59 to 75, 77, 80, 81, 83 to 88, 90 to 94, 96 to 104, 107, 109, 110, 112 to 114, 116 to 122, 124 to 129, 131 to 144, 147 to 164, and 165 it was 30% or less than that on an untreated plant.

Test Example 8

[002258] Each of the plastic pots was filled with sandy clay and barley (cultivar. MIKAMO GOLDEN) was sown and cultivated in a greenhouse for 7 days. Each of the present compounds 12, 17, 36, 51.58, 79, 106, 166 to 181.206, 208 to 210, and 215 to 217 was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the stems and leaves of the barley so that they are sufficiently adhered to the surface of the leaves of the barley. After vaporization, the plant was dried by air. After 2 days, an aqueous suspension containing barley spot fungus spores (Pirenophora teres) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to rest for 3 days in a greenhouse at 23 ° C during the day and 20 ° C during the night under high humidity conditions and grown in a greenhouse for 7 days, and then the injury spots was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 12, 17, 36, 51, 58, 79, 106, 166 to 181, 206, 208 to 210, and 215 to 217 was 30 % or less than that on an untreated plant.

Test Example 9

[002259] Each of the plastic pots was filled with sandy clay and common beans (cultivar. NAGAUZURA NATAN E) was sown and cultivated in a greenhouse for 8 days. Each of the present compounds 4, 5, 8, 15, 18 to 21, 27, 39, 45, 46, 50, 54, 55, 59, 60, 65, 70, 74, 75, 77, 79 to 84, 90 at 94, 97 at 99, 101 at 103, 116 at 122, 125, 126, 144, 160 at 162, and 164 was diluted with water to adjust to a predetermined concentration of 500 ppm. The diluted solution obtained was sprayed on the stems and leaves of the common bean so that it was sufficiently adhered to the surface of the leaves of the common bean. After vaporization, the plant was air-dried and a PDA medium containing hyphae of the common bean stem rot fungus (Sclerotinia sclerotiorum) was placed on the leaves of the common bean. After inoculation, all common beans were allowed to rest under high humidity condition only at night. Four days after inoculation, the lesion spot area was investigated. As a result, the area of lesion spots on a plant treated with any of the present compounds 4, 5, 8, 15, 18 to 21, 27, 39, 45, 46, 50, 54, 55, 59, 60, 65, 70, 74, 75, 77, 79 to 84, 90 to 94, 97 to 99, 101 to 103, 116 to 122, 125, 126, 144, 160 to 162, and 164 was 30% or less than that on an untreated plant.

Test Example 10

[002260] Each of the plastic pots was filled with sandy clay and common beans (cultivar. NAGAUZURA NATANE) was sown and cultivated in a greenhouse for 8 days. Each of the present compounds 6, 14, 40, 48, 58, 69, 138, 139, 168, 169, 171, 174, 178, 206, and 210 was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the stems and leaves of the common bean so that it was sufficiently adhered to the surface of the leaves of the common bean. After vaporization, the plant was air-dried and a PDA medium containing hyphae of the common bean stem rot fungus (Sclerotinia sclerotiorum) was placed on the leaves of the common bean. After inoculation, all common beans were allowed to rest under high humidity condition only at night. Four days after inoculation, the lesion spot area was investigated. As a result, the area of lesion spots on a plant treated with any of the present compounds 6, 14, 40, 48, 58, 69, 138, 139, 168, 169, 171, 174, 178, 206, and 210 it was 30% or less than that on an untreated plant.

Test Example 11

[002261] Each of the plastic pots was filled with sandy clay and wheat (cultivar.APOGEE) was sown and cultivated in a puff for 10 days. Each of the present compounds 1 to 8, 10, 11, 13 to 15, 18 to 23, 25, 26, 37, 39 to 50, 52 to 62, 64 to 70, 72 to 75, 78, 82, 84 to 87 , 90 to 94, 96 to 98, 100 to 103, 109 to 113, 116 to 122, 124 to 127, 131, 134 to 137, 139 to 141, 149, 150, 152, 153, 157, 161, 162, 164 , and 165 was diluted with water to adjust to a predetermined concentration of 500 ppm. The diluted solution obtained was sprayed on the wheat stems and leaves so that it was sufficiently adhered to the surface of the wheat leaves. After vaporization, the plant was dried by air. After 4 days, an aqueous suspension containing spores of wheat leaf pustule fungus (Septoria tritici) was sprayed to inoculate the spores. After the inoculation was completed, the plant was allowed to rest at 18 ° C under high humidity for 3 days and allowed to remain under illumination for 14 to 18 days, and then the lesion spot area was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 1 to 8, 10, 11, 13 to 15, 18 to 23, 25, 26, 37, 39 to 50, 52 to 62, 64 to 70, 72 to 75, 78, 82, 84 to 87, 90 to 94, 96 to 98, 100 to 103, 109 to 113, 116 to 122, 124 to 127, 131, 134 to 137, 139 to 141, 149, 150, 152, 153, 157, 161, 162, 164, and 165 was 30% or less than that on an untreated plant.

Test Example 12

[002262] Each of the plastic pots was filled with sandy clay and wheat (cultivar.APOGEE) was sown and cultivated in a puff for 10 days. Each of the present compounds 16, 27, 31, 32, 35, 38, 51, 77, 80, 95, 99, 104, 114, 128, 138, 142, 143, 145, 146, 148, 151, 154 to 156 , 158, 159, 163, 166, 168 to 181, 206, 208 to 210, and 215 to 217 were diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the wheat stems and leaves so that it was sufficiently adhered to the surface of the wheat leaves. After vaporization, the plant was dried by air. After 4 days, an aqueous suspension containing spores of wheat leaf pustule fungus (Septoria tritici) was sprayed to inoculate the spores. After the inoculation was completed, the plant was allowed to rest at 18 ° C under high humidity for 3 days and allowed to remain under illumination for 14 to 18 days, and then the lesion spot area was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 16, 27, 31, 32, 35, 38, 51, 77, 80, 95, 99, 104, 114, 128, 138, 142, 143, 145, 146, 148, 151, 154 to 156, 158, 159, 163, 166, 168 to 181, 206, 208 to 210, and 215 to 217 was 30% or less than that on a non-plant treated.

Test Example 13

[002263] Each of the plastic pots was filled with sandy clay and wheat (cultivar.APOGEE) was sown and cultivated in a greenhouse for 10 days. Then, an aqueous suspension containing spores of wheat leaf pustule fungus (Septoria tritici) was sprayed on the wheat to inoculate the spores. The plant was allowed to rest at 18 ° C under high humidity for 3 days and air dried. Each of the present compounds 2, 4 to 6, 8, 11, 13 to 15, 19, 23, 37, 39 to 44, 46, 48, 49, 55 to 58, 60, 65, 66, 68 to 70, 72 , 73, 92, 93, 98, 101, 102, 112, 116, 117, 119, 120, 122, 124 to 126, 128, 131, 134, 136, 137, 139 to 141, 153, 154, 157, 169 at 172, 174, 175, 177 to 181, 206, 209, 210, and 215 to 217 was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the wheat stems and leaves so that it was sufficiently adhered to the surface of the wheat leaves. After vaporization, the plant was air-dried and also left to remain under lighting for 14 to 18 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 2, 4 to 6, 8, 11, 13 to 15, 19, 23, 37, 39 to 44, 46, 48, 49, 55 to 58, 60, 65, 66, 68 to 70, 72, 73, 92, 93, 98, 101, 102, 112, 116, 117, 119, 120, 122, 124 to 126, 128, 131, 134, 136, 137, 139 to 141, 153, 154, 157, 169 to 172, 174, 175, 177 to 181, 206, 209, 210, and 215 to 217 was 30% or less than that on an untreated plant.

Test Example 14

[002264] Each of the plastic pots was filled with sandy clay and cucumber {cultivar. SAGAMI HANJIRO) was sown and grown in a greenhouse for 12 days. Each of the present compounds 1 to 8, 11, 13 to 15, 18 to 23, 27, 37 to 50, 52, 53, 55 to 60, 65, 66, 68 to 70, 72, 74, 77, 91, 93 , 94, 97 to 99, 102, 103, 109, 111, 116 to 122, 124 to 128, 131, 132, 136 to 141, 144, 149 to 154, 157, 159, 163, 164, and 165 were diluted with water to adjust to a predetermined concentration of 500 ppm. The diluted solution obtained was sprayed on the stems and leaves of the cucumber so that it was sufficiently adhered to the surface of the leaves of the cucumber. After vaporization, the plant was air-dried and then inoculated by sprinkling with fungus spores from the dusty cucumber mold (Sphaerotheca fuliginea, a Qol-resistant strain in which, among the genes encoding cytochrome b, the amino acid residue at position 143 of cytochrome b it is mutated from glycine to alanine). After inoculation, the plant was grown in a greenhouse at 24 ° C during the day and 20 ° C at night for 8 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 1 to 8, 11, 13 to 15, 18 to 23, 27, 37 to 50, 52, 53, 55 to 60, 65, 66, 68 to 70, 72, 74, 77, 91, 93, 94, 97 to 99, 102, 103, 109, 111, 116 to 122, 124 to 128, 131, 132, 136 to 141, 144, 149 to 154, 157, 159, 163, 164, and 165 was 30% or less than that on an untreated plant.

Test Example 15

[002265] Each of the plastic pots was filled with sandy clay and soy (cultivar. KUROSENGOKU) was sown and cultivated in a greenhouse for 13 days. Each of the present compounds 11, 12, 19, 39, 57, 58, 65, 69, 70, 74, 98, 104, 119, 122, 137, 140, 141, 143, 144, 157, 161, 169, 170 , 172, 178, and 179 was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the soybean stems and leaves so that they are sufficiently adhered to the surface of the soybean leaves. After vaporization, the plant was dried by air. After 2 days, an aqueous suspension containing soybean rust fungus spores (Phakopsora pachyrhizi) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to rest for 3 days in a greenhouse at 23 ° C during the day and 20 ° C during the night under high humidity condition and grown in a greenhouse for 14 days, and then the injury spots was investigated. As a result, it was discovered that the area of lesion spots on the plant treated with each of the present compounds 11, 12, 19, 39, 57, 58, 65, 69, 70, 74, 98, 104, 119, 122 , 137, 140, 141, 143, 144, 157, 161, 169, 170, 172, 178, and 179 was 30% or less than that on an untreated plant.

Test Example 16

[002266] Each of the plastic pots was filled with sandy clay and barley (cultivar. MIKAMO GOLDEN) was sown and cultivated in a greenhouse for 7 days. Each of the present compounds 1 to 8, 11, 13 to 23, 27, 32, 35, 37, 39 to 42, 44 to 46, 48 to 50, 53 to 60, 62, 64 to 66, 68 to 70, 72 74, 83 to 85, 88, 90 to 95, 97 to 104, 107, 110 to 112, 114 to 122, 124 to 126, 128, 131, 134, 136 to 141, 143, 144, 146, 148 to 150 , 152 to 155, 157, 159, 161 to 163, 164, 166 to 181, 206, 208 to 210, and 215 to 217 were diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the stems and leaves of the barley so that they are sufficiently adhered to the surface of the leaves of the barley. After vaporization, the plant was dried by air. After 2 days, an aqueous suspension containing barley-burning fungus spores (Rhynchosporium secalis) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to rest for 3 days in a greenhouse at 23 ° C during the day and 20 ° C during the night under high humidity conditions and grown in a greenhouse for 7 days, and then the injury spots was investigated. As a result, it was discovered that the area of lesion spots on the plant treated with each of the present compounds 1 to 8, 11, 13 to 23, 27, 32, 35, 37, 39 to 42, 44 to 46, 48 to 50, 53 to 60, 62, 64 to 66, 68 to 70, 72 to 74, 83 to 85, 88, 90 to 95, 97 to 104, 107, 110 to 112, 114 to 122, 124 to 126, 128 , 131, 134, 136 to 141, 143, 144, 146, 148 to 150, 152 to 155, 157, 159, 161 to 163, 164, 166 to 181, 206, 208 to 210, and 215 to 217 was 30% or less than that on an untreated plant.

Test Example 17

[002267] Each of the plastic pots was filled with sandy clay and tomato (cultivar.PATIO) was sown and cultivated in a greenhouse for 20 days, the present compound 57 was diluted with water to adjust to a predetermined concentration of 500 ppm. The diluted solution obtained was sprayed on the stems and leaves of the tomato seedling so that it was sufficiently adhered to the surface of the tomato seedling leaves. After vaporization, the plant was dried by air. After 2 days, an aqueous suspension containing spores of late tomato fungus (Phytophthora infestans) was sprayed to inoculate the spores. After completion of inoculation, the seedling was first allowed to rest at 23 ° C under high humidity for one day and then grown in an air-conditioned room at 20 ° C for 4 days. Then, the area of lesion spots was investigated. As a result, it was found that the area of lesion spots on a plant treated with the present compound 57 was 30% or less than that on an untreated plant.

Test Example 18

[002268] Each of the plastic pots was filled with sandy clay and cucumber (cultivar. SAGAMI HANJIRO) was sown and cultivated in a greenhouse for 19 days. Each of the present compounds 4 to 6, 11, 13, 14, 19 to 23, 25 to 32, 35, 37 to 41, 46, 48, 50, 52, 55 to 62, 64 to 66, 68 to 70, 72 to 74, 76, 78 to 80, 86, 87, 92, 98 to 103, 149, 152, 157, 158, 166 to 174, 176 to 181, 206, 208 to 210, 215, and 217 was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the stems and leaves of the cucumber so that it was sufficiently adhered to the surface of the leaves of the cucumber. After vaporization, the plant was dried by air. After one day, the plant was inoculated by spraying with fungus spores from the cucumber corynespora leaf spot (Corynespora cassico / a). After inoculation, the plant was grown in a greenhouse at 24 ° C during the day and 20 ° C at night for 7 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 4 to 6, 11, 13, 14, 19 to 23, 25 to 32, 35, 37 to 41, 46, 48, 50, 52, 55 to 62, 64 to 66, 68 to 70, 72 to 74, 76, 78 to 80, 86, 87, 92, 98 to 103, 149, 152, 157, 158, 166 to 174, 176 to 181, 206, 208 to 210, 215, and 217 was 30% or less than that on an untreated plant.

Test Example 19

[002269] Each of the plastic pots was filled with sandy clay and cucumber (cultivar.SAGAMI HANJIRO) was sown and cultivated in a greenhouse for 19 days. Each of the present compounds 4, 5, 8, 11, 13 to 16, 18, 19, 21, 23, 26, 31, 35, 37, 39, 40, 44 to 46, 48, 50, 55 to 60, 62 , 65, 67 to 70, 72 to 74, 92, 93, 96, 98, 100, 102, 103, 112, 116 to 120, 122, 124 to 127, 129, 131, 132, 134, 136 to 143, 145 , 147, 148, 152, 157, 166 to 170, 172, 174, 176, 178 to 180, 208 to 210, and 217 was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the stems and leaves of the cucumber so that it was sufficiently adhered to the surface of the leaves of the cucumber. After vaporization, the plant was dried by air. After one day, the plant was inoculated by spraying with spores of cucumber anthracnose fungus (Colletotrichum lagenarium). After inoculation, the plant was first allowed to rest at 23 ° C under high humidity for one day and then grown in a greenhouse at 24 ° C during the day and 20 ° C at night for 6 days. Then, the area of lesion spots was investigated. As a result, the area of lesion spots on the plant treated with each of the present compounds 4, 5, 8, 11, 13 to 16, 18, 19, 21, 23, 26, 31, 35, 37, 39, 40, 44 to 46, 48, 50, 55 to 60, 62, 65, 67 to 70, 72 to 74, 92, 93, 96, 98, 100, 102, 103, 112, 116 to 120, 122, 124 to 127, 129, 131, 132, 134, 136 to 143, 145, 147, 148, 152, 157, 166 to 170, 172, 174, 176, 178 to 180, 208 to 210, and 217 was 30% or less of than the one about an untreated plant.

Test Example 20

[002270] Each of the present compounds 44, 111, 119, 122, 128, 134, 135, 139, 142, 143, 159, and 165 was diluted with deionized water to adjust to a predetermined concentration of 500 ppm, thereby obtaining a chemical test solution.

[002271] Thirty (30) heads of cotton aphids (Aphis gossypii) (including adults and larvae) were released on the leaves of cucumber {cultivar. SAGAMI HANJIRO FUSHINARI) grown in a polyethylene cup until the first real leaf is developed. The next day, 20 ml of the chemical test solution mentioned above were sprayed. After 6 days, the number of surviving insects was counted and the control value was calculated using the following equation: Control value (%) = {1 - (Cb x Tai) / (Cai x Tb)} x 100

[002272] where the symbols in the equation represent the following:

[002273] Cb: number of insects before vaporizing the chemical solution in the untreated area;

[002274] Cai: number of insects surviving in the untreated area;

[002275] Tb: number of insects before vaporizing the chemical solution in the treated area; and

[002276] Tai: number of insects surviving in the treated area.

[002277] As a result, the present compound 44, 111, 119, 122, 128, 134, 135, 139, 142, 143, 159, or 165 showed 90% or more of the control value.

Test Example 21

[002278] Each of the present compounds 23, 60, 66, and 73 was diluted with deionized water to adjust to a predetermined concentration of 500 ppm, thereby obtaining a chemical test solution.

[002279] The chemical test solution mentioned above (0.7 ml) was added to 100 ml of deionized water to adjust an active ingredient concentration to 3.5 ppm. Twenty (20) heads of last instar larvae of the common household mosquito (Culex pipiens pallens) were released into the solution and the number of dead insects was counted after 8 days.

[002280] Mortality was determined by the following equation: Mortality (%) = (number of dead insects / number of test insects) x 100

[002281] As a result, the present compound 23, 60, 66, or 73 exhibited 100% mortality.

Test Example 22

[002282] Each of the present compounds 25, 52, and 120 was diluted with deionized water to adjust to a predetermined concentration of 500 ppm, thereby obtaining a chemical test solution.

[002283] Cabbage (cultivar. GREEN BALL) was planted in each of the polyethylene cups and cultivated until the third real leaf or the fourth real leaf develops. The aforementioned chemical test solution was sprayed on the cabbage at a rate of 20 mL / cup. After drying the chemical solution, the polyethylene cup having a diameter of 5.5 cm was covered with a filter paper deposited on the base, the cabbage cut from the root was placed and 5 heads of third instar larvae of cabbage moth ( Plutella xylostella) were released into the cup and the cup was covered with the lid. The cup was kept at 25 ° C and, after 5 days, the number of surviving insects was counted and insect mortality was calculated using the following equation: Mortality (%) = (number of dead insects / number of test insects) x 100

[002284] As a result, the present compound 25, 52, or 120 exhibited mortality of 80% or more.

Test Example 23

[002285] The present compound 67 was diluted with deionized water to adjust to a predetermined concentration of 500 ppm, thereby obtaining a chemical test solution.

[002286] On each of the polyethylene cups having a diameter of 5.5 cm, a filter paper having the same size was deposited. The aforementioned test chemical solution (0.7 ml) was dripped onto the filter paper and 30 mg of sucrose were placed as bait. Two (2) heads of an adult male German cockroach (Blattella germanica) were released into the polyethylene cup and the cup was covered with the lid. After 6 days, the life or death of a German cockroach was investigated and mortality was determined by the following equation: Mortality (%) = (number of dead insects / number of test insects) x 100

[002287] As a result, the present compound 67 exhibited 100% mortality.

Test Example 24

[002288] Each of the present compounds 19, 20, 28, 29, and 52 was diluted with deionized water to adjust to a predetermined concentration of 500 ppm, thereby obtaining a chemical test solution.

[002289] The chemical test solution mentioned above (0.7 ml_) was added to 100 ml of deionized water to adjust an active ingredient concentration to 3.5 ppm. Twenty (20) heads of last instar larvae of the common household mosquito (Culex pipiens pallens) were released into the solution and, after one day, the number of dead insects was counted.

[002290] Mortality was determined by the following equation: Mortality (%) = (number of dead insects / number of test insects) x 100

[002291] As a result, the present compounds 19, 20, 28, 29, and 52 exhibited 100% mortality.

Test Example 25

[002292] The present compound 52 was diluted with deionized water to adjust to a predetermined concentration of 500 ppm, thereby obtaining a chemical test solution.

[002293] On each of the polyethylene cups having a diameter of 5.5 cm, a filter paper having the same size was deposited. Insecta LF (manufactured by NOSAN CORPORATION) was chopped 6 mm thick, cut in half, and then placed on the filter paper. Then, 2 ml of the test chemical solution was poured into the polyethylene cup. After air drying, 5 heads of third instar larvae of common caterpillar (Spodoptela litura) were released into the polyethylene cup and the cup was sealed with a lid. After 6 days, the number of dead insects was counted. Mortality was calculated according to the following equation: Mortality (%) = (number of dead insects / number of test insects) x 100

[002294] As a result, the present compound 52 exhibited 100% mortality.

Test Example 26

[002295] The present compound 52 was diluted with deionized water to adjust to a predetermined concentration of 500 ppm, thereby obtaining a chemical test solution.

[002296] In each of the polyethylene cups having a diameter of 5.5 cm, a filter paper having the same size was deposited. Silkmate 2S (manufactured by NOSAN CORPORATION) was chopped at 2 mm thick, and then placed on the filter paper. Then, 1 ml of the chemical test solution was poured into the polyethylene cup. After air drying, 30 heads of first instar larvae of apple root knot nematode (Adoxophyes orana) were released into the polyethylene cup and the cup was sealed with a lid. After 7 days, the number of dead insects was counted. Mortality was calculated according to the following equation: Mortality (%) = (number of dead insects / number of test insects) x 100

[002297] As a result, the present compound 52 exhibited 100% mortality.

Comparative Example 1

[002298] Each of the plastic pots was filled with sandy clay and barley (cultivar. MIKAMO GOLDEN) was sown and cultivated in a greenhouse for 7 days. A 1-methyl-4- [2- (6-phenyl pyridin-2-yloxymethyl) -phenyl] -1,4-dihydrotetrazol-5-one control compound was diluted with water to adjust to a predetermined concentration of 3.1 ppm. The diluted solution obtained was sprayed on the stems and leaves of the barley so that it was sufficiently adhered to the surface of the leaves of the barley. After vaporization, the plant was dried by air. After 2 days, an aqueous suspension containing barley spot fungus spores (Pirenophora teres) was sprayed to inoculate the spores. After completion of inoculation, the plant was allowed to rest for 3 days in a greenhouse at 23 ° C during the day and 20 ° C during the night under high humidity conditions and grown in a greenhouse for 7 days, and then the injury spots was investigated. As a result, it was found that the lesion spot area on a plant treated with the control compound 1-methyl-4- [2- (6-phenylpyridin-2-yloxymethyl) -phenyl] -1,4-di- hydrotetrazol-5-one was 70% or more than that in an untreated plant.

Comparative Example 2

[002299] Each of the plastic pots was filled with sandy clay and cucumber (cultivar.SAGAMI HANJIRO) was sown and cultivated in a greenhouse for 12 days. A control compound 1- [2- (biphenyl-3-yloxymethyl) -phenyl] -4-methyl-1,4-dihydrotetrazol-5-one was diluted with water to adjust to a predetermined concentration of 200 ppm. The diluted solution obtained was sprayed on the stems and leaves of the cucumber so that it was sufficiently adhered to the surface of the leaves of the cucumber. After vaporization, the plant was air-dried and then inoculated by sprinkling with fungus spores from the dusty cucumber mold (Sphaerotheca fuliginea, a Qol-resistant strain in which, among the genes encoding cytochrome b, the amino acid residue in position 143 of cytochrome b is mutated from glycine to alumina). After inoculation, the plant was grown in a greenhouse at 24 ° C during the day and 20 ° C at night for 8 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on a plant treated with the control compound 1 - [2- (biphenyl-3-yloxymethyl) -phenyl] -4-methyl-1,4-dihydrotetrazol-5-one was 70% or more than that on an untreated plant.

[002300] The present compound has pest control activity and is useful as an active ingredient in a pest control agent.

Claims (33)

1. Tetrazolinone compound characterized by the fact that it is represented by formula (1):

wherein R1 and R2 represent a hydrogen atom; R3 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a halogen atom, or a C1-C6 alkoxy group; R4, R5, and R6 represent a hydrogen atom; R7 represents a C1-C3 alkyl group or a hydrogen atom; A represents a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, a C2-C9 heterocyclyl group optionally having one or more atoms or groups selected from Group P (as long as the C2-C9 heterocyclyl group has, as a ring constituent atom, one or two atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, and when the C2-C9 heterocyclyl group has two atoms selected from the group consisting of an atom of nitrogen, an oxygen atom, and a sulfur atom, each atom can be equal to, or different from, the other group, and also the carbon or nitrogen atom that constitutes the ring of the heterocyclic C2-C9 group is attached to Q) , or a C3-C12 cycloalkenyl group (provided that the C6-C16 aryl group and the C2-C9 heterocyclyl group optionally have one or more atoms or groups selected from Group P and, when these groups have two or more atoms or groups selected Group P, each atom or group can be equal to, or different from at least one other atom or group); Q represents the following group Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, or Q12 {the symbol # represents an A binding site, and the symbol • represents a binding site to an oxygen atom};

R8, R9, R1 0, R1 1, R1 2, R1 3, R1 4, R1 5, R1 6, R1 7, R1 8 R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R3 \ R32, R33, R34, R35, and R36 each independently represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group; and X represents an oxygen atom or a sulfur atom: Group P: Group consisting of a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 group haloalkoxy, a C1-C6 alkylthio group, a C2-C6 alkylcarbonyl group, a formyl group, a nitro group, a cyano group, a C6-C16 aryl group, a C6-C16 aryloxy group, a C1-C6 alkylsulfonyl group, a amino group optionally having a C1-C6 alkyl group, and an aminocarbonyl group 2. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q1. 3. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q2. 4. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q3. 5. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q4. 6. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q5. 7. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q6. 8. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q7. 9. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q8. 10. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q9. 11. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q10. 12. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q11. 13. Tetrazolinone compound according to claim 1, characterized by the fact that Q is Q12. 14. A tetrazolinone compound according to any one of claims 1 to 13, characterized in that R7 is a methyl group; and X is an oxygen atom. 15. A tetrazolinone compound according to any one of claims 1 to 14, characterized in that A is a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P (provided that when the group C6-C16 aryl has two or more atoms or groups selected from Group P, each atom or group can be equal to, or different from at least one other atom or group). 16. Tetrazolinone compound according to any one of claims 1 to 15, characterized in that A is of formula (2):

wherein R37, R38, R39, R40, and R41 each independently represent a halogen atom, a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1 group -C6 haloalkoxy, a C1-C6 alkylthio group, a C2-C6 alkylcarbonyl group, a formyl group, a nitro group, a cyano group, a C6-C16 aryl group, a C6-C16 aryloxy group a C1-C6 alkylsulfonyl group, . 17. Tetrazolinone compound according to any one of claims 1,2, 14, 15, or 16, characterized by the fact that Q is Q1; R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, or a C1-C3 alkoxy group; R37, R38, R39, R40, and R41 each independently represent a halogen atom, a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 group haloalkoxy, a C1-C6 alkylthio group, a formyl group, a C2-C6 alkylcarbonyl group, a nitro group, a cyano group, a C6-C16 aryloxy group, a C1-C6 alkylsulfonyl group, or an aminocarbonyl group. 18. A tetrazolinone compound according to any one of claims 1,2, and 14 to 17, characterized in that: R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, or a C1-C3 alkoxy group; and R37, R38, R39, R40, and R41 each independently represent a halogen atom, a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, or a C1 group -C3 haloalkoxy. 19. Tetrazolinone compound according to any one of claims 1,2, and 14 to 18, characterized in that: R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, an ethyl group , or a methoxy group; R37 is a methoxy group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a bromine atom; and R38, R39, R40, and R41 each independently represent a hydrogen atom or a fluorine atom. 20. Tetrazolinone compound according to any one of claims 1, 3, 14, 15, and 16, characterized by the fact that Q is Q2; R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom, or a C1-C3 alkoxy group; R11, R12, R13 and R14 each independently represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 alkoxy group; R37, R38, R39, R40, and R41 each independently represent a halogen atom, a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 group haloalkoxy, a C1-C6 alkylthio group, a formyl group, a C2-C6 alkylcarbonyl group, a nitro group, a cyano group, a C6-C16 aryloxy group, a C1-C6 alkylsulfonyl group, or an aminocarbonyl group. 21. The tetrazolinone compound according to any one of claims 1,3, 14 to 16, and 20, characterized in that: R3 is a C1-C3 alkyl group, a C3-C4 cycloalkyl group, a halogen atom or a C1-C3 alkoxy group; and R37, R38, R39, R40, and R41 each independently represent a halogen atom, a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 alkoxy group, or a C1 group -C3 haloalkoxy. 22. Tetrazolinone compound according to any one of claims 1,3, 14 to 16, 20, and 21, characterized in that: R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom , an ethyl group, or a methoxy group; R37 is a methoxy group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a bromine atom; and R38, R39, R40, and R41 each independently represent a hydrogen atom or a fluorine atom. 23. The tetrazolinone compound according to any one of claims 1 to 14, characterized in that A is a C2-C9 heterocyclyl group optionally having one or more atoms or groups selected from Group P as long as the C2-C9 heterocyclyl group has , as a ring constituent atom, one or two atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom, and when the C2-C9 heterocyclyl group has two atoms selected from the group consisting of one nitrogen atom, an oxygen atom, and a sulfur atom, each atom can be equal to, or different from, the other atom, and the carbon or nitrogen atom that makes up the ring of the C2-C9 heterocyclyl group is attached to Q, or a C3-C12 cycloalkenyl group, provided that when the C2-C9 heterocyclyl group has two or more atoms or groups selected from Group P, each atom or group can be equal to, or different from, at least one other atom or group . 24. Tetrazolinone compound according to any one of claims 1 to 14, characterized in that A is a C2-C9 heteroaryl group optionally having one or more atoms or groups selected from Group P, provided that the C2-C9 heteroaryl group has, as a constituent atom of the ring, one or two atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom and when the C2-C9 heteroaryl group has two atoms selected from the group consisting of an atom of nitrogen, an oxygen atom and a sulfur atom, each atom can be the same or different from the other atom, and the carbon or nitrogen atom that constitutes the C2-C9heterocyclyl ring is linked to Q, as long as the C2 group -C9 heteroaryl optionally has one or more atoms or groups selected from the group P and, when those groups have two or more atoms or groups selected from the group P, each atom or group can be the same or different from at least one other tome or group. 25. Plant disease control agent, characterized in that it comprises the tetrazolinone compound as defined in any one of claims 1 to 24. 26. Method for the control of plant disease, characterized in that it comprises treating plants or soil with an effective amount of the tetrazolinone compound as defined in any one of claims 1 to 24. 27. Use of the tetrazolinone compound as defined in any of claims 1 to 24, characterized in that it is for the control of plant disease. 28. Tetrazolinone compound, characterized by the fact that it is: 1 -2- (6-bromopyridin-2-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazole-5-one

1 - [2- (2-bromopyridin-6-yloxymethyl) -3-cyclopropylphenyl] -4-methyl-1,4-dihydrotetrazole-5-one

1 - [2- (2-bromopyl rid i n-6-i loxy methyl I) -3-ethyl Ifenyl] -4-methyl I-1,4-dihydrotetrazol-5-one

1 - [2- (2-bromopyridin-6-yloxymethyl) -3-chlorophenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (2-bromopyridin-6-yloxymethyl) -3-methoxyphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (5-bromo-2-methylphenoxymethyl) -3-methoxyphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (3-bromophenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (3-bromo-2-fluorophenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (3-bromo-4-methylphenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (5-bromo-2-chlorophenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (5-bromo-2-fuorophenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (3-bromo-4-methoxyphenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (3-bromo-5-methylphenoxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (3-bromo-4-fluorophenoxy methyl) -3-methyl Ifenyl] -4-methyl I-1,4-dihydrotetrazol-5-one

1 - [2- (6-chloropyrimidin-4-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (6-Chloropyrazin-2-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (4-Bromopyridin-2-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (5-bromopyridin-3-yloxyethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazole-5-one

1 - [2- (2-C loropyl rid i n-4-i loxy methyl I) -3-methyl Ifenyl] -4-methyl I-1,4-dihydrotetrazol-5-one

1 - [2- (2-Chloropyrimidin-4-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1 - [2- (4-Chloropyrimidin-2-yloxymethyl) -3-methylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

1- [2- (4-chloro-1,3,5-triazin-2-yloxymethyl) -3-meylphenyl] -4-methyl-1,4-dihydrotetrazol-5-one

29. Tetrazolinone compound according to any one of claims 1,2, and 14 to 18, characterized in that: R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, an ethyl group , or a methoxy group; R37 is a methoxy group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, or a bromine atom; R38, R39, and R40 each independently represent a hydrogen atom or a fluorine atom; and R41 is a hydrogen atom, a methoxy group, or an ethoxy group. 30. Tetrazolinone compound according to any one of claims 1, 2, 14, and 24, characterized by the fact that Q is Q1; and A is formula (4):

wherein R42, R43, R44, and R45 each independently represent a halogen atom, a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6 group haloalkoxy, a C1-C6 alkylthio group, a C2-C6 alkylcarbonyl group, a formyl group, a nitro group, a cyano group, a C6-C16 aryl group, a C6-C16 aryloxy group, a C1-C6 alkylsulfonyl group or aminocarbonyl group. 31. Tetrazolinone compound according to any one of claims 1, 2, 14, 24, and 30, characterized in that R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, a group ethyl, or a methoxy group; R42 is a hydrogen atom, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, or a trifluoromethyl group; R43 and R44 each independently represent a hydrogen atom or a fluorine atom; and R45 is a hydrogen atom, a methoxy group, or an ethoxy group. 32. Tetrazolinone compound according to any one of claims 1, 3, 14, and 24, characterized by the fact that Q is Q2; and A is of formula (4). 33. Tetrazolinone compound according to any one of claims 1, 3, 14, 24, and 32, characterized in that: R3 is a methyl group, a cyclopropyl group, a chlorine atom, a bromine atom, a ethyl group, or a methoxy group; R42 is a hydrogen atom, a methoxy group, an ethoxy group, a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, or a trifluoromethyl group; R43 and R44 each independently represent a hydrogen atom or a fluorine atom; and R45 is a hydrogen atom, a methoxy group, or an ethoxy group.